Water → alpha-t-Butyloxycarbonylamino-alpha-[2-(chloroacetamido)thiazol-4-yl]acetic acid ethyl ester

HRID 1395413Notes

Reaction equation

HRID 1395413 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)[CH3:2].[Cl:21][CH2:22][C:23](Cl)=[O:24].O>CN(C)C(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1[N:7]=[C:8]([NH:11][C:23](=[O:24])[CH2:22][Cl:21])[S:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 12763199alpha-t-Butyloxycarbonylamino-alpha-(2-aminothiazol-4-yl)acetic acid ethyl ester

Product 1

HCID 12763202alpha-t-Butyloxycarbonylamino-alpha-[2-(chloroacetamido)thiazol-4-yl]acetic acid ethyl esterYield 90.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1.26 g of α-t-butyloxycarbonylamino-α-(2-aminothiazol-4-yl)acetic acid ethyl ester in 5 ml of N,N-dimethylacetamide is added 708 mg of chloroacetyl chloride under stirring. After the stirring for further 1 hour at room temperature, the reaction solution is poured into water and extracted with ethyl acetate. The organic layer is washed with saturated sodium bicarbonate aq. solution and then water and dried over anhydrous magnesium sulfate. The distillation of the solvent gives 1.435 g of α-t-butyloxycarbonylamino-α-[2-(chloroacetamido)thiazol-4-yl]acetic acid ethyl ester as crystals (yield, 90.8%). Melting point: 192°-193° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with saturated sodium bicarbonate aq. solution
  3. dry with materialwater and dried over anhydrous magnesium sulfate
  4. distillationThe distillation of the solvent
  5. customgives

Sources & evidence

ORD record
ord-d4895006eb6b4f9a8c9f9c809e339a9d
Source dataset
uspto-grants-1980_05
Patent number
US04203899

Reaction notes

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