Water → HCID 12805053, compound

HRID 1380223Notes

Reaction equation

HRID 1380223 reaction equation
[C:1]1([CH:7]([O:14][C:15](=[O:35])[C@H:16]([N:21]2[C:27](=[O:28])[C@H:26]3[C@@H:22]2[O:23][C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:25]3)[C:17]([CH2:19]I)=[CH2:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:36]>>[C:1]1([CH:7]([O:14][C:15](=[O:35])[C@H:16]([N:21]2[C:27](=[O:28])[C@H:26]3[C@@H:22]2[O:23][C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:25]3)[C:17]([CH2:19][OH:36])=[CH2:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 962WaterHCID 13276941HCID 13276941, compound

Product 1

HCID 12805053HCID 12805053, compound

Procedure

To a mixture of (2R)-2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-3-iodomethyl-3-butenoic acid diphenylmethyl ester (1) in an organic solvent and inorganic base in water is added a peracid portionwise under nitrogen gas, and the mixture is stirred for the given time at the given temperature under nitrogen. The reaction mixture is washed with water, aqueous 5% sodium thiosulfate, aqueous sodium hydrogen carbonate and water, dried over sodium sulfate and concentrated under reduced pressure. The residue is crystallized from ethanol to give (2R)-2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]-hept-2-en-6-yl]-3-hydroxymethyl-3-butenoic acid diphenylmethyl ester (2). mp. 100°-104° C.

Workup

  1. washThe reaction mixture is washed with water, aqueous 5% sodium thiosulfate, aqueous sodium hydrogen carbonate and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-6c6f01b951684e288d494f85a161c7fa
Source dataset
uspto-grants-1986_04
Patent number
US04581173

Reaction notes

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