Benzyl chloroformate → 2-(2-{[(Benzyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetic acid

HRID 586361Notes

Reaction equation

HRID 586361 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1.[OH-].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O1CCOCC1.C(OCC)C>[CH2:17]([O:16][C:14]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acid

Product 1

HCID 223217672-(2-{[(Benzyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetic acidYield 41%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

(2-Aminothiazol-4-yl)acetic acid (10 g, 63.2 mmol) was dissolved in 1,4-dioxane (100 mL) and aqueous NaOH (6 M, 100 mL), and the solution was cooled to 0° C. Benzyl chloroformate (20 mL, 82.2 mmol) was added, and the mixture was stirred at room temperature overnight. The mixture was diluted with diethyl ether, and the layers separated. The water layer was cooled to 0° C., and the pH adjusted to approximately 4 with aqueous HCl (6 M). The white precipitate formed was collected by vacuum filtration, washed with water and diethyl ether, and dried under vacuum to provide (2-benzyloxycarbonylaminothiazol-4-yl)acetic acid (7.5 g, 41%).

Workup

  1. customthe layers separated
  2. temperatureThe water layer was cooled to 0° C.
  3. customThe white precipitate formed
  4. filtrationwas collected by vacuum filtration
  5. washwashed with water and diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-495c441b29e549598509a798454d6f33
Source dataset
uspto-grants-2005_08
Patent number
US06936611B2

Reaction notes

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