Benzene → HCID 86737050, compound

HRID 1706534Notes

Reaction equation

HRID 1706534 reaction equation
C(OC([NH:8][CH:9]([C:39]([O:41]CC1C=CC(OC)=CC=1)=[O:40])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:35](=[O:38])[CH:36]=[O:37])[CH:20]2[CH2:23][N:22]([CH:24]([C:31]([OH:33])=[O:32])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]2=[O:34])=[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:39]([OH:41])=[O:40])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]([C:35](=[O:38])[CH:36]=[O:37])[CH:20]2[CH2:23][N:22]([CH:24]([C:31]([OH:33])=[O:32])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]2=[O:34])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86737051HCID 86737051, compound

Product 1

HCID 86737050HCID 86737050, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 3-[4-{3-tert-butoxycarbonylamino-3-(4-methoxybenzyloxycarbonyl)propoxy}phenylglyoxyloylamino]-1-(α-carboxybenzyl)-2-azetidinone (870 mg), benzene (4 ml) and anisol (1 ml), there was added 2,2,2-trifluoroacetic acid (2 ml) under ice-cooling. The mixture was stirred at the same temperature for 1.5 hours and then diethyl ether (50 ml) was added thereto. The mixture was stirred for half an hour and insoluble materials were collected by filtration and suspended in ethyl acetate (30 ml). After the suspension was stirred at ambient temperature for half an hour, insoluble materials were collected by filtration and then treated with diethyl ether to give 3-[4-(3-amino-3-carboxypropoxy)phenylglyoxyloylamino]-1-(α-carboxybenzyl)-2-azetidinone (0.52 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for half an hour
  3. filtrationinsoluble materials were collected by filtration
  4. stirringAfter the suspension was stirred at ambient temperature for half an hour
  5. filtrationinsoluble materials were collected by filtration
  6. additiontreated with diethyl ether

Sources & evidence

ORD record
ord-1eab1a79af0046d4a342ca5d97c650c7
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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