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 1444568Notes

Reaction equation

HRID 1444568 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-yl-propionic 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-yl-propionic 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-89325d271fe545099f6af9ee5e95a187
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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