2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 10974502, compound

HRID 863357Notes

Reaction equation

HRID 863357 reaction equation
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH3:15][N:16]([CH3:67])[C:17]([C@H:19]1[N:23]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])[CH2:22][C@@H:21]([S:37][C:38]2[C@H:39]([CH3:66])[C@@H:40]3[C@@H:57]([C@H:58]([O:60][Si](C)(C)C)[CH3:59])[C:56](=[O:65])[N:41]3[C:42]=2[C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[CH2:20]1)=[O:18]>CO>[CH3:67][N:16]([CH3:15])[C:17]([C@H:19]1[N:23]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])[CH2:22][C@@H:21]([S:37][C:38]2[C@H:39]([CH3:66])[C@@H:40]3[C@@H:57]([C@H:58]([OH:60])[CH3:59])[C:56](=[O:65])[N:41]3[C:42]=2[C:43]([O:45][CH2:46][C:47]2[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=2)=[O:44])[CH2:20]1)=[O:18]

Participants

4

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 10327839HCID 10327839, compound

Product 1

HCID 10974502HCID 10974502, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8 mg (0.039 mmol) of citric acid hydrate were added to 2 ml of a solution containing 55 mg of 4-nitrobenzyl (1R,5S,6S)-2-[(3S,5S)-5-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-3-pyrrolidinylthio]-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 18)in methanol, and the resulting mixture was stirred at room temperature for 35 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through 5 g of silica gel, using a 1:9 by volume mixture of methanol and ethyl acetate as the eluent, to give 42 mg (yield 84%) of the title compound as a vitreous solid.

Workup

  1. customprepared
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. customthe residue was purified by column chromatography through 5 g of silica gel
  4. additionby volume mixture of methanol and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-e85a6a6b421d4f53b84dd42a7b00a4d9
Source dataset
uspto-grants-1998_02
Patent number
US05719275

Reaction notes

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