Methanol → 4-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

HRID 863354Notes

Reaction equation

HRID 863354 reaction equation
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH2:15]([N:17]([CH2:56][CH3:57])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:27]1[C@H:28]([CH3:55])[C@@H:29]2[C@@H:46]([C@H:47]([O:49][Si](C)(C)C)[CH3:48])[C:45](=[O:54])[N:30]2[C:31]=1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])=[O:19])[CH3:16].CO>C(Cl)Cl>[CH2:56]([N:17]([CH2:15][CH3:16])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:27]1[C@H:28]([CH3:55])[C@@H:29]2[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:54])[N:30]2[C:31]=1[C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)=[O:33])=[O:19])[CH3:57]

Participants

5

Reactant 3

HCID 887MethanolHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 99607884-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

Product 1

HCID 570929914-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylateYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

41 mg (0.195 mmol) of citric acid hydrate were added to 30 ml of a solution of 1.072 g (1.71 mmol) of 4-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 34) in a 2:1 by volume mixture of methanol and methylene chloride, and the mixture was stirred for 20 minutes at room temperature. At the end of this time, the reaction solution was condensed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 25 g of silica gel. Elution with ethyl acetate afforded 970 mg (quantitative yield) of the title compound as a colorless foam-like solid.

Workup

  1. customcondensed
  2. distillationby distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through 25 g of silica gel
  4. washElution with ethyl acetate

Sources & evidence

ORD record
ord-384317453601467f999890daf25fc78a
Source dataset
uspto-grants-1998_02
Patent number
US05719275

Reaction notes

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