2-Tert-butoxycarbonylamino-3-thiazol-2-ylpropionic acid methyl ester → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acid

HRID 1985783Notes

Reaction equation

HRID 1985783 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

Reactant 1

HCID 673920652-Tert-butoxycarbonylamino-3-thiazol-2-ylpropionic acid methyl ester

Product 1

HCID 11184857(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acidYield 42.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

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 6N 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

  1. additionwas added Alcalase (2.4 L, 0.08 mL)
  2. customThe reaction mixture was then evaporated at 30° C.
  3. customto remove acetonitrile
  4. washthe aqueous residue was washed with ether
  5. extractionthe solution was extracted with ethyl acetate
  6. customThe combined organic layers were then dried
  7. customevaporated

Sources & evidence

ORD record
ord-4ceff010c6bc4d3b96d43903351266ff
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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