Benzene → HCID 86736763, compound

HRID 2051696Notes

Reaction equation

HRID 2051696 reaction equation
C(OC([NH:8][CH:9]([C:38]([OH:40])=[O:39])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:34](=[O:37])[CH:35]=[O:36])[CH:20]2[CH2:23][N:22]([CH:24]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[C:25]([OH:27])=[O:26])[C:21]2=[O:33])=[CH:15][CH:14]=1)=O)(C)(C)C.C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(OCC)C>[NH2:8][CH:9]([C:38]([OH:40])=[O:39])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:34](=[O:37])[CH:35]=[O:36])[CH:20]2[CH2:23][N:22]([CH:24]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[C:25]([OH:27])=[O:26])[C:21]2=[O:33])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86736761HCID 86736761, compound

Product 1

HCID 86736763HCID 86736763, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-[3-{4-(3-tert-Butoxycarbonylamino-3-carboxypropoxy)phenylglyoxyloylamino}-2-oxo-1-azetidinyl]-2-(2-thienyl)acetic acid (0.830 g.) was added to a mixture of benzene (4 ml.) and anisol (1 ml.), and to the mixture, there was added 2,2,2-trifluoroacetic acid (2 ml.) under ice-cooling. The mixture was stirred at the same temperature for 2.5 hours, and diethyl ether (50 ml.) was added to the reaction mixture, whereafter the stirring was continued under ice-cooling for half an hour. Insoluble materials were collected by filtration and suspended in ethyl acetate (30 ml.). The suspention was stirred for an hour, whereafter the insoluble materials were collected by filtration, washed with diethyl ether and then dried to give 2-[3-{4-(3-amino-3-carboxypropoxy)phenylglyoxyloylamino}-2-oxo-1-azetidinyl]-2-(2-thienyl)acetic acid (0.49 g.).

Workup

  1. temperaturecooling
  2. temperaturecooling for half an hour
  3. filtrationInsoluble materials were collected by filtration
  4. stirringThe suspention was stirred for an hour, whereafter the insoluble materials
  5. filtrationwere collected by filtration
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-50629031cdf94ab38719ed2e8248afd8
Source dataset
uspto-grants-1980_01
Patent number
US04181800

Reaction notes

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