2-Tert-butoxycarbonylamino-3-thiazol-2-ylpropionic acid methyl ester → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acid
Reaction equation
C[O:2][C:3](=[O:19])[CH:4]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1>C(#N)C.C([O-])(O)=O.[Na+]>[C:15]([O:14][C:12]([NH:11][C@@H:4]([CH2:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1)[C:3]([OH:19])=[O:2])=[O:13])([CH3:18])([CH3:16])[CH3:17]Participants
4
Procedure
To 2-tert-butoxycarbonylamino-3-thiazol-2-ylpropionic acid methyl ester (500 mg, 1.75 mmol) in a mixture of acetonitrile (6 mL) and 0.2 M aqueous NaHCO3 (12 mL) was added Alcalase (2.4 L, 0.08 mL), and the solution was stirred vigorously at room temperature for about 2.5 h. The reaction mixture was then evaporated at 30° C. to remove acetonitrile, and the aqueous residue was washed with ether. The aqueous phase was acidified with 6 N HCl to pH 3 and the solution was extracted with ethyl acetate. The combined organic layers were then dried and evaporated to yield 2(S)-tert-butoxycarbonylamino-3-thiazol-2-ylpropionic acid (204 mg).
Workup
- additionwas added Alcalase (2.4 L, 0.08 mL)
- customThe reaction mixture was then evaporated at 30° C.
- customto remove acetonitrile
- washthe aqueous residue was washed with ether
- extractionthe solution was extracted with ethyl acetate
- customThe combined organic layers were then dried
- customevaporated
Sources & evidence
- ORD record
- ord-5278f9f0def04cecb0265400d0adbc10
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737300B2
Reaction notes
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