Sodium Hydroxide → (3S)-3-[[[2-(formylamino)-4-thiazolyl]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid
Reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][C:10]([OH:12])=O)[N:8]=1)=[O:2].[NH2:13][C@H:14]1[CH:17]([CH3:18])[N:16]([S:19]([OH:22])(=[O:21])=[O:20])[C:15]1=[O:23].[OH-].[Na+]>>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][C:10]([NH:13][C@H:14]2[CH:17]([CH3:18])[N:16]([S:19]([OH:22])(=[O:20])=[O:21])[C:15]2=[O:23])=[O:12])[N:8]=1)=[O:2]Participants
Procedure
100 mg. of a Escherichia coli acylase that is bound in a polyacrylamide matrix (Boehringer Mannheim) is mixed with an aqueous solution containing 4 mg. of 2-(formylamino)-4-thiazoleacetic acid and an aqueous solution containing 2 mg. of (3S)-3-amino-4-methyl-2-oxo-1-azetidinesulfonic acid, inner salt in a total volume of 2 ml. The pH of the reaction mixture is adjusted to pH 4.5 by the addition of 50 mmolar sodium hydroxide. The reaction mixture is incubated at 30° C. with shaking (60 rpm) for up to 20 hours. The desired product can then be separated from the reaction mixture by thin layer chromatography using a silica gel 60 F254 plate and developing in a solvent consisting of acetonitrile, ethyl acetate, acetic acid, and water (4:4:1:1) followed by elution with water to give (3S)-3-[[[2-(formylamino)-4-thiazolyl]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, zwitterion.
Workup
- additionis mixed with an aqueous solution
- additioncontaining 4 mg
- customis incubated at 30° C.
- customThe desired product can then be separated from the reaction mixture by thin layer chromatography
- washfollowed by elution with water
Sources & evidence
- ORD record
- ord-e701070d876943f79be34d059d844e0b
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04596777
Reaction notes
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