Process for microbially oxidizing n-substituted glucamines
AssigneeG. D. Searle & Co.
InventorsROY WALTER GRABNER, BRYAN HAYDEN LANDIS, PING TU WANG, MICHAEL LEE PRUNIER, MIKE G. SCAROS
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Abstract
The invention is a process for producing N-substituted glucamines, a process for oxidizing an N-substituted glucamine with an oxidizing microbe or extract thereof, and a process for oxidizing an N-substituted glucamine with an oxidizing microbe or extract thereof and reducing the oxidized N-substituted glucamine to an N-substituted-1-deoxynojirimycin. In addition, a one pot process for producing N-substituted-1-deoxynojirimycin from D-glucose is disclosed.
Claims88
A process which comprises oxidizing a glucamine of the formula:
- 5
- or salts thereof, with an oxidizing microbe or extract thereof, and producing a compound of the formula:
- 6
- wherein R is phenyl, C1-C10 alkyl, C1-C10 alkyl substituted with phenyl or carboxy, or C2-C10 alkyl substituted with hydroxy.
A process which comprises oxidizing a glucamine of the formula:
- 7
- or salts thereof, wherein R is phenyl, C1-C10 alkyl, C1-C10 alkyl substituted with phenyl or carboxy, or C2-C10 alkyl substituted with hydroxy, with an oxidizing microbe or extract thereof, and producing a compound of the formula:
- 8
- wherein R is as described above, and then reducing said compound to produce N-substituted-1-deoxynojirimycin of the formula:
- 9
- wherein R is as described above.
A process which comprises amination of D-glucose to an N-substituted glucamine of the formula:
- 10
- or salts thereof, wherein R is phenyl, C1-C10 alkyl, C1-C10 alkyl substituted with phenyl or carboxy, or C2-C10 alkyl substituted with hydroxy, with an oxidizing microbe or extract thereof, and producing a compound of the formula:
- 11
- wherein R is as described above, and then reducing said compound to produce N-substituted-1-deoxynojirimycin of the formula:
- 12
- wherein R is as described above.
A process which comprises:
- (a) mixing a solvent and amine
- (b) adjusting the pH to about 8.0 to 12.0,
- (c) adding D-glucose in about a 1:1 ratio with the amine,
- (d) adding a catalyst,
- (e) reducing at about 1 to 100 atm at about 25° C. to 100° C.,
- (f) removing the catalyst,
- (g) adjusting the pH to about 1 to 7, and
- (h) removing the solvent to obtain an N-substituted glucamine salt.
A process which comprises:
- (a) mixing ethanol and n-butylamine,
- (b) adjusting the pH to about 9-11 with hydrochloric acid,
- (c) adding D-glucose in about a 1:1 ratio with n-butylamine,
- (d) adding a palladium on carbon catalyst,
- (e) reducing at about 1 to 5 atm at about 40° C. to 80° C.,
- (f) removing the catalyst,
- (g) adjusting the pH to about 5.5 with hydrochloric acid, and
- (h) removing the ethanol to obtain N-n-butyl glucamine.
The compound 6-n-butylamino-6-deoxy-α-L-sorbofuranose.
The salt form of the compound 6-n-butylamino-6-deoxy-α-L-sorbofuranose.
Dependencies are inferred from the claim text.