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

HRID 223628Notes

Reaction equation

HRID 223628 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-048d96ea09974d35b07d799a12f03db9
Source dataset
uspto-grants-1982_10
Patent number
US04355160

Reaction notes

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