Benzene → HCID 86736763, compound

HRID 1659517Notes

Reaction equation

HRID 1659517 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-eb31dee14fb9451486606b24cf701e74
Source dataset
uspto-grants-1981_12
Patent number
US04304718

Reaction notes

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