Propionic Acid → HCID 131710649, compound

HRID 436270Notes

Reaction equation

HRID 436270 reaction equation
[C:1](O)(=[O:4])CC.[OH:6][C:7]([CH2:41]Br)=[C:8]([N:12]1[C:15](=[O:16])[CH:14]([NH:17][C:18](=[O:37])[CH:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:13]1[S:38]C=O)[C:9]([O-:11])=[O:10].[C:43]1([CH3:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:24]([O:23][C:21]([NH:20][CH:19]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:18]([NH:17][CH:14]1[C:15](=[O:16])[N:12]2[C:8]([C:9]([O:11][CH2:49][C:43]3[CH:48]=[CH:47][C:46]([O:4][CH3:1])=[CH:45][CH:44]=3)=[O:10])=[C:7]([OH:6])[CH2:41][S:38][C@H:13]12)=[O:37])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 1140Toluene2×HCID 178526148HCID 178526148, compound

Product 1

HCID 131710649HCID 131710649, compound

Conditions

Temperature
15 °C

Procedure

To 0.430 g. (1.1 mmol.) of mercuric acetate in a mixture of 20 ml. of toluene and 10 ml. of propionic acid are added 0.632 g. (1 mmol.) of 3-hydroxy-4-bromo-2-[2-formylthio-4-oxo-3-(α-benzyloxycarbonylaminophenylacetamido)-1-azetidinyl]-2-butenoate, p-methoxybenzyl ester, in 20 ml. of toluene. The mixture is stirred for 30 minutes at 15° C., after which time the solution becomes cloudy. Hydrogen sulfide is bubbled into the mixture, and the mixture then is filtered through activated charcoal and a filter aide. The resulting filtrate is evaporated, and a residue comprising p-methoxybenzyl 7-(α-benzyloxycarbonylaminophenylacetamido)-3-hydroxy-3-cephem-4-carboxylate is obtained.

Workup

  1. customHydrogen sulfide is bubbled into the mixture
  2. filtrationthe mixture then is filtered through activated charcoal
  3. customThe resulting filtrate is evaporated

Sources & evidence

ORD record
ord-32c9a8920fd84f9e978a584cda95256a
Source dataset
uspto-grants-1977_02
Patent number
US04008230

Reaction notes

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