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

HRID 2287178
Notes
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Reaction equation

HRID 2287178 reaction equation
[C:1]([CH:11]1[O:17][CH:16]2[CH:13]([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][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.[C:34]1([CH2:40][C:41](Cl)=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>O1CCCC1>[C:1]([CH:11]1[O:17][CH:16]2[C:13]([C:41](=[O:42])[CH2:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 70561235Methyl alpha-(3xi-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetate

Product 1

HCID 131711533Methyl alpha-(3xi-carbobenzoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetate
Yield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.90 g of methyl α-(3ξ-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 50 ml of tetrahydrofuran are added 2.4 ml of triethylamine and then 2.5 ml of phenylacetyl chloride under ice-cooling, and the mixture stirred for 30 minutes, poured into water and extracted with ethyl acetate. The extract is washed with water dried on magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on 150 g of silica gel containing 10% water and eluted with benzene containing 10% ethyl acetate to yield 4.37 g of methyl α-(3ξ-carbobenzoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 67.2% yield.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on 150 g of silica gel containing 10% water
  6. washeluted with benzene containing 10% ethyl acetate

Sources & evidence

ORD record
ord-901b31c4601d4608a822b14fd47692f4
Source dataset
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04269773

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes