Acetic Acid → HCID 20445641, compound

HRID 1706527Notes

Reaction equation

HRID 1706527 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:8]([N:10]([CH:19]1[CH2:22][N:21]([CH:23]([C:27]([OH:29])=[O:28])[CH:24]([CH3:26])[CH3:25])[C:20]1=[O:30])C(OCC(Cl)(Cl)Cl)=O)=[O:9])[NH2:7].C(O)(=O)C>CN(C)C=O.[Zn]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:8]([NH:10][CH:19]1[CH2:22][N:21]([CH:23]([C:27]([OH:29])=[O:28])[CH:24]([CH3:26])[CH3:25])[C:20]1=[O:30])=[O:9])[NH2:7]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20445649HCID 20445649, compound

Product 1

HCID 20445641HCID 20445641, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

3-[2-(2-Thienyl)-N-(2,2,2-trichloroethoxycarbonyl)glycinamido]-1-(1-carboxy-2-methylpropyl)-2-azetidinone (1.0 g.) was dissolved in N,N-dimethylformamide (5 ml.), and acetic acid (3 ml.) was added thereto. To the solution, there was added zinc powder (1.2 g.) at 15° C. in the course of about half an hour, whereafter the mixture was stirred at 15° to 20° C. for 3 hours. The unreacted zinc powder was filtered off and washed with a small amount of N,N-dimethylformamide, and then this washings and the filtrate were combined. Diethyl ether (about 80 ml.) was added to the combined solution and the precipitating materials were collected by filtration, washed with diethyl ether and then dried to give 3-[2-(2-thienyl)glycinamido]-1-(1-carboxy-2-methylpropyl)-2-azetidinone (690 mg.).

Workup

  1. filtrationThe unreacted zinc powder was filtered off
  2. washwashed with a small amount of N,N-dimethylformamide
  3. additionDiethyl ether (about 80 ml.) was added to the combined solution
  4. filtrationthe precipitating materials were collected by filtration
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-b7ab625250e2469f960cba28fae4eeef
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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