Citric Acid → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acid

HRID 1039034Notes

Reaction equation

HRID 1039034 reaction equation
C([O:8][C:9](=[O:25])[C@@H:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][C:12]1[S:13][CH:14]=[CH:15][N:16]=1)C1C=CC=CC=1.O1CCCC1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:21]([O:20][C:18]([NH:17][C@@H:10]([CH2:11][C:12]1[S:13][CH:14]=[CH:15][N:16]=1)[C:9]([OH:25])=[O:8])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 672357662-(S)-tert-butoxycarbonylamino-3-thiazol-2-yl-propionic acid benzyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask was charged with 2-(S)-tert-butoxycarbonylamino-3-thiazol-2-yl-propionic acid benzyl ester (370 mg, 1.02 mmol), tetrahydrofuran (9.0 mL), water (0.9 mL), and lithium hydroxide (48 mg, 1.14 mmol) and the resulting mixture was stirred at room temperature for 6 h. The resulting mixture was then neutralized with 10% citric acid and extracted with ethyl acetate (100 mL), and dichlormethane (100 mL). The organic layers were dried with MgSO4, filtered, and concentrated in vacuo to yield (S)-2-(tert-butoxycarbonylamino)-3-(thiazol-2-yl)propanoic acid. MS (ES+) 273 (M+1).

Workup

  1. extractionextracted with ethyl acetate (100 mL), and dichlormethane (100 mL)
  2. dry with materialThe organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17928a82399a4df9afee440ba3d4cbd1
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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