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US 8,293,926 B2Granted
Method of producing optically active 4-amino-3-substituted phenylbutanoic acid
AssigneeSumitomo Chemical Company, Limited
InventorsJunichi Yasuoka, Shoji Fukuyo, Tetsuya Ikemoto
Life of this patent
Estimating the term…
Abstract
The present invention provides a method of producing a compound (IIa) or a compound (IIb), provides a method of producing a compound (IIIa) or a compound (IIIb), provides a method of producing a compound (Va) or its salt or a compound (Vb) or its salt, provides a method of producing a compound (IIIa) or a compound (IIIb), further, provides a method of producing a compound (Va) or its salt or a compound (Vb) or its salt including these production methods.
Claims39
A method comprising dissolving or dispersing a compound of the formula (IIIa):
- (wherein, n represents an integer of 0 to 3, R1 represents a halogen atom, alkyl group, alkoxy group, haloalkyl group and cycloalkyloxy group, when n is 2 or 3, R1s may be the same or different, or when n is 2 or 3, two R1s together form an alkylenedioxy group, R2 represents an alkyl group) or a compound of the formula (IIIb):
- (wherein, R1, R2 and n have the same meanings as described above)
- in a solvent, and adding the resultant solution or dispersion to an acid, to produce a compound of the formula (Va):
- (wherein, R1, R2 and n have the same meanings as described above);
- and
- wherein the reduction of a compound of the formula (IIa) or a compound of the formula (IIb) is catalytic hydrogen reduction in the presence of a developed nickel containing iron.
3 more elements
A method comprising catalytic hydrogen reduction and cyclization of a compound of the formula (IIa):
- (wherein, n represents an integer of 0 to 3, R1 represents a halogen atom, alkyl group, alkoxy group, haloalkyl group and cycloalkyloxy group, when n is 2 or 3, R1s may be the same or different, or when n is 2 or 3, two R1s together form an alkylenedioxy group, R2 represents an alkyl group) or a compound of the formula (IIb):
- (wherein, R1, R2 and n have the same meanings as described above)
- in the presence of a developed nickel containing iron, to produce a compound of the formula (IIIa):
- (wherein, R1, R2 and n have the same meanings as described above) or a compound of the formula (IIIb):
- (wherein, R1, R2 and n have the same meanings as described above).
2 more elements
A method of producing a compound of the formula (Va) or its salt or a compound of the formula (Vb) or its salt, comprising
- a step of catalytic hydrogen reduction and cyclization of a compound of the formula (IIa):
- (wherein, n represents an integer of 0 to 3, R1 represents a halogen atom, alkyl group, alkoxy group, haloalkyl group and cycloalkyloxy group, when n is 2 or 3, R1s may be the same or different, or when n is 2 or 3, two R1s together form an alkylenedioxy group, R2 represents an alkyl group) or a compound of the formula (IIb):
- (wherein, R1, R2 and n have the same meanings as described above)
- in the presence of a developed nickel containing iron, to produce a compound of the formula (IIIa):
- (wherein, R1, R2 and n have the same meanings as described above) or a compound of the formula (IIIb):
- (wherein, R1, R2 and n have the same meanings as described above);
- a step of hydrolysis and decarboxylation of the compound of the formula (IIIa) or the compound of the formula (IIIb), to obtain a compound of the formula (IVa):
- (wherein, R1 and n have the same meanings as described above) or a compound of the formula (IVb):
- (wherein, R1 and n have the same meanings as described above);
- and
- a step of ring-opening the compound of the formula (IVa) or the compound of the formula (IVb), to obtain a compound of the formula (Va):
- (wherein, R1 and n have the same meanings as described above) or its salt or a compound of the formula (Vb):
- (wherein, R1 and n have the same meanings as described above) or its salt.
10 more elements
A method of producing a compound of the formula (Va) or its salt, comprising
- a step of reacting a compound of the formula (I):
- (wherein, n represents an integer of 0 to 3, R1 represents a halogen atom, alkyl group, alkoxy group, haloalkyl group and cycloalkyloxy group, when n is 2 or 3, R1s may be the same or different, or when n is 2 or 3, two R1s together form an alkylenedioxy group)
- with a compound of the formula (I′):
- CH2(CO2R2)2
- (wherein, R2 represents an alkyl group)
- in the presence of nickel(II)bis[(S,S)—N,N′-dibenzylcyclohexane-1,2-diamine]bromide, to obtain a compound of the formula (IIa):
- (wherein, R1, R2 and n have the same meanings as described above);
- a step of reducing and cyclizing the compound of the formula (IIa) to obtain a compound of the formula (IIIa):
- (wherein, R1, R2 and n have the same meanings as described above);
- and
- a step of dissolving or dispersing the compound of the formula (IIIa) in a solvent, and adding the resultant solution or dispersion to an acid, to obtain a compound of the formula (Va):
- (wherein, R1 and n have the same meanings as described above) or its salt.
9 more elements
Dependencies are inferred from the claim text.