Methyl alpha-(3xi-carbobenzoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetate → Methyl alpha-(3xi-carboxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetate

HRID 971412Notes

Reaction equation

HRID 971412 reaction equation
[C:1]([CH:11]1[O:17][CH:16]2[C:13]([C:27](=[O:35])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:14](=[O:26])[N:15]2[C:18](=[C:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[NH:12]1)([O:3]CC1C=CC=CC=1)=[O:2]>O1CCCC1.[C].[Pd]>[C:1]([CH:11]1[O:17][CH:16]2[C:13]([C:27](=[O:35])[CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:14](=[O:26])[N:15]2[C:18](=[C:23]([CH3:24])[CH3:25])[C:19]([O:21][CH3:22])=[O:20])[NH:12]1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 131711533Methyl alpha-(3xi-carbobenzoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetate

Product 1

HCID 131711536Methyl alpha-(3xi-carboxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetateYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.24 g of methyl α-(3ξ-carbobenzoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate dissolved in 64 ml of tetrahydrofuran is catalytically hydrogenated on 1.3 g of 5% palladium carbon under atmospheric pressure. The catalyst is removed by filtration and the filtrate is condensed to yield 3.38 g of methyl α-(3ξ-carboxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate as crude product in quantitative yield.

Workup

  1. customThe catalyst is removed by filtration
  2. customcondensed

Sources & evidence

ORD record
ord-c32d0340563c48439dc48a2e8e30ac89
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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