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Oxygen → Benzyl alpha-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-hydroxyethylidene)acetate

HRID 67854
Notes
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Reaction equation

HRID 67854 reaction equation
[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:30])[N:13]2[CH:16]([C:27]([CH3:29])=C)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:31]=O.CSC>ClCCl.CO>[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:30])[N:13]2[C:16](=[C:27]([OH:31])[CH3:29])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 13578824HCID 13578824, compound

Product 1

HCID 70503985Benzyl alpha-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-hydroxyethylidene)acetateYield 70.28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of benzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-isopropenylacetate (4.22 g) in dichloromethane and methanol (5:1) is introduced ozonized oxygen until the blue color of the solution does not fade out. Then the solution is mixed with dimethyl sulfide, washed with water, dried, and concentrated. The obtained residue is purified by chromatography over silica gel containing 10% water to give benzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate (2.98 g: 70.28%).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe obtained residue is purified by chromatography over silica gel containing 10% water

Sources & evidence

ORD record
ord-786f62b9112e48f2833ff8a45c1be0bc
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04346218

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes