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US 6,784,293 B1Granted
Process for making Boc-protected 3-aminohydantoins/thiohydantoins and 3-aminodihydrouracils/dihydrothiouracils
AssigneeThe Procter & Gamble Company
InventorsShengde Wu, John Michael Janusz
Life of this patent
Estimating the term…
Abstract
The present invention provides a process for the efficient assembly of Boc-protected 3-aminohydantoins/thiohydantoins and 3-aminodihydrouracils/dihydrothiouracils via a one-pot solution phase or solid phase synthesis from readily available starting materials.
Claims25
A method for making a hydantoin or thiohydantoin having the formula:
- wherein X is oxygen or sulfur, R1 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- R2 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- said method comprising the steps of:
- a) reacting a hydrazine compound having the formula:
- with an amino acid ester having the formula:
- R is alkyl, carbocyclic ring, heterocyclic ring, aromatic ring, or heteroaromatic ring, to form a reaction mixture;
- and
- b) heating said reaction mixture to form said hydantoin or thiohydantoin.
5 more elements
A method for making a 3-aminodihydrouracil or 3-aminodihydrothiouracil having the formula:
- wherein X is oxygen or sulfur, R1 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- R2 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- or R1 and the member carbon atom adjacent to the carbon atom containing R2 can be taken together to form a ring system;
- said ring system being carbocyclic ring, heterocyclic ring, or heteroaromatic ring;
- said method comprising the steps of:
- a) reacting a hydrazine compound having the formula:
- with an amino acid ester having the formula:
- R is alkyl, carbocyclic ring, heterocyclic ring, aromatic ring, heteroaromatic ring, to form a reaction mixture;
- and
- b) heating said reaction mixture to form said 3-aminodihydrouracil or 3-aminodihydrothiouracil.
7 more elements
A method for making a hydantoin or thiohydantoin having the formula:
- wherein X is oxygen or sulfur, R1 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- R2 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- or R1 and R2 can be taken together to form a carbocyclic ring, heterocyclic ring, with the hydantoin a heteroaromatic ring with the hydantoin or;
- said method comprising the steps of:
- a) relating a hydrazine compound having the formula:
- with a resin-bound amino acid ester having the formula
- wherein the symbol:
- signifies a Merrifield resin, hydroxymethyl, resin, Wang resin, or PEG resin:
- to form a reaction mixture;
- and
- b) heating said reaction mixture to form said hydantoin or thiohydantoin.
8 more elements
A method for making a 3-aminodihydrouracil or 3-aminodihydrothiouracil having the formula:
- wherein X is oxygen or sulfur, R1 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- R2 is hydrogen, alkyl, a heterocyclic ring, an aromatic ring, or a heteroaromatic ring;
- or R1 and the member carbon atom adjacent to the carbon atom containing R2 can be taken together to form a carbocylic ring, heterocyclic ring, a with the 3-aminodihydrouracil or 3-heteroaromatic ring with the 3-aminodihydrouracil or;
- said method comprising the steps of:
- a) reacting a hydrazine compound having the formula:
- with an amino acid ester having the formula:
- wherein the symbol:
- signifies a Merrifield resin, hydroxymethyl, resin, Wang resin, or PEG resin;
- to form a reaction mixture;
- and
- b) heating said reaction mixture to form said 3-aminodihydrouracil or 3-aminodihydrothiouracil.
8 more elements
Dependencies are inferred from the claim text.