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 907598Notes

Reaction equation

HRID 907598 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-1700e3dc0ac148e89b9ce3c953039cdf
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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