Water → HCID 131711550, compound

HRID 2287193Notes

Reaction equation

HRID 2287193 reaction equation
Cl[CH2:2][C:3]([CH:5]1[O:11][CH:10]2[C:7]([C:33](=[O:41])[CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:8](=[O:32])[N:9]2[C:12](=[C:29]([CH3:31])[CH3:30])[C:13]([O:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[NH:6]1)=[O:4].O>C(O)(=O)C.[Zn]>[C:3]([CH:5]1[O:11][CH:10]2[C:7]([C:33](=[O:41])[CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:8](=[O:32])[N:9]2[C:12](=[C:29]([CH3:31])[CH3:30])[C:13]([O:15][CH:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[NH:6]1)(=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 131711543HCID 131711543, compound

Product 1

HCID 131711550HCID 131711550, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1.59 g of diphenylmethyl α-(3ξ-chloroacetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 16 ml of acetic acid is added 1.5 g of zinc powder, and the mixture stirred at room temperature for 1 hour, then poured into water and extracted with methylene chloride. The extract is washed with water, dried on magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on 30 g of silica gel containing 10% water and eluted with benzene containing 10% ethyl acetate to yield 1.21 g of diphenylmethyl α-(3ξ-acetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 81% yield.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract is washed with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on 30 g of silica gel containing 10% water
  6. washeluted with benzene containing 10% ethyl acetate

Sources & evidence

ORD record
ord-b718e68d67694198a596970f70ef8bae
Source dataset
uspto-grants-1981_05
Patent number
US04269773

Reaction notes

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