Diethyl Ether → HCID 86739640, compound

HRID 2418200Notes

Reaction equation

HRID 2418200 reaction equation
C(OC([NH:8][CH:9]([C:48]([OH:50])=[O:49])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[N:46][OH:47])[C:20]([NH:22][CH:23]2[CH2:26][N:25]([CH:27]([C:42]([OH:44])=[O:43])[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:30][CH:29]=3)[C:24]2=[O:45])=[O:21])=[CH:15][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)C>C1C=CC=CC=1>[NH2:8][CH:9]([C:48]([OH:50])=[O:49])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[N:46][OH:47])[C:20]([NH:22][CH:23]2[CH2:26][N:25]([CH:27]([C:42]([OH:44])=[O:43])[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:30][CH:29]=3)[C:24]2=[O:45])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 86739641HCID 86739641, compound

Product 1

HCID 86739640HCID 86739640, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-[2-{4-(3-tert-Butoxycarbonylamino-3-carboxypropoxy)phenyl}-2-hydroxyiminoacetamido]-1-(α-carboxy-4-benzyloxybenzyl)-2-azetidinone (240 mg) was suspended in benzene (2 ml), and to the suspension, there was added 2,2,2-trifluoroacetic acid (0.5 ml) at 7° C. with stirring. The mixture was stirred at the same temperature for 2 hours, and diethyl ether (about 25 ml) was added to the reaction mixture, and then the precipitating crystals were collected by filtration. The crystals were suspended in ethyl acetate and then the suspension was stirred at ambient temperature for half an hour. The crystals were collected by filtration and washed with diethyl ether to give 3-[2-{4-(3-amino-3-carboxypropoxy)phenyl}-2-hydroxyiminoacetamido]-1-(α-carboxy-4-benzyloxybenzyl)-2-azetidinone (180 mg), mp 164° to 167.5° C.

Workup

  1. stirringThe mixture was stirred at the same temperature for 2 hours
  2. filtrationthe precipitating crystals were collected by filtration
  3. stirringthe suspension was stirred at ambient temperature for half an hour
  4. filtrationThe crystals were collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-0b55c4fa93b7430b86bd4745167505c2
Source dataset
uspto-grants-1984_09
Patent number
US04472300

Reaction notes

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