Acetone → HCID 131712368, compound

HRID 1577157Notes

Reaction equation

HRID 1577157 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:48])[C:15]([C:23]3[N:24]=[C:25]([NH:28][C:29]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[S:26][CH:27]=3)=[N:16][O:17]C(C)(OC)C)[C:11](=[O:49])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].C(NCC)C.CC(C)=O.Cl>O>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:48])[C:15]([C:23]3[N:24]=[C:25]([NH:28][C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[S:26][CH:27]=3)=[N:16][OH:17])[C:11](=[O:49])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 131712369HCID 131712369, compound

Product 1

HCID 131712368HCID 131712368, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21 g of the product of Step A, 80 ml of acetone and 27 ml of 2 N hydrochloric acid was stirred at room temperature for 90 minutes and 55 ml of water were added thereto with stirring. The acetone was evaporated under reduced pressure and 140 ml of ethyl acetate were added with stirring. The decanted aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with half saturated aqueous sodium chloride solution, was dried and vacuum filtered to obtain the syn isomer of 3-methyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. stirringwith stirring
  2. customThe acetone was evaporated under reduced pressure and 140 ml of ethyl acetate
  3. additionwere added
  4. stirringwith stirring
  5. extractionThe decanted aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phases were washed with half saturated aqueous sodium chloride solution
  7. customwas dried
  8. filtrationvacuum filtered

Sources & evidence

ORD record
ord-8a50d5dde54d4037acc1f7a1547b8444
Source dataset
uspto-grants-1981_09
Patent number
US04287193

Reaction notes

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