Water → p-Nitrobenzyl(5RS,6SR)-3-[(Z)-2-Acetamidoethenylthio]-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1632870

Reaction equation

HRID 1632870 reaction equation
[N+:1]([C:4]1[CH:45]=[CH:44][C:7]([CH2:8][O:9][C:10]([O:12][CH:13]([CH:15]2[C:21](=[O:22])[N:20]3[CH:16]2[CH2:17][C:18]([S:36]([C:38]2N=CC=CN=2)=O)=[C:19]3[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH2:46]>ClCCl.[Cl-].C([N+](C)(C)CCCCCCCCCCCCCCCC)C1C=CC=CC=1>[C:19]([NH:20]/[CH:16]=[CH:38]\[S:36][C:18]1[CH2:17][CH:16]2[N:20]([C:21](=[O:22])[CH:15]2[CH:13]([O:12][C:10]([O:9][CH2:8][C:7]2[CH:44]=[CH:45][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[CH3:14])[C:19]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:46])[CH3:18]

Participants

5

Reactant 2

HCID 962WaterHCID 20442568p-Nitrobenzyl(5RS,6SR)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-3-(2-pyrimidylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 88723757p-Nitrobenzyl(5RS,6SR)-3-[(Z)-2-Acetamidoethenylthio]-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 52%

Reagents, catalysts & solvents 2

HCID 31202Benzylhexadecyldimethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Nitrobenzyl(5RS,6SR)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-3-(2-pyrimidylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (230 mg) in dichloromethane (25 ml) was treated with benzyldimethyl-n-hexadecylammonium chloride (12 mg), cooled in an ice-bath, and treated with sodium Z-2-acetamidoethenylthiolate (contanimated by 1 molar equivalent NaCl) (77 mg) in water (25 ml). After stirring vigorously for 25 min. the layers were separated, and the dichloromethane layer was washed with dilute aqueous NaHCO3, followed by brine. After drying (MgSO4) the solution was evaporated in vacuo and the residue was chromatographed on silica gel (230-400 mesh ASTM), eluting with ethyl acetate to give the title compound (118 mg, 52% yield).

Workup

  1. temperaturecooled in an ice-bath
  2. customwere separated
  3. washthe dichloromethane layer was washed with dilute aqueous NaHCO3
  4. dry with materialAfter drying (MgSO4) the solution
  5. customwas evaporated in vacuo
  6. customthe residue was chromatographed on silica gel (230-400 mesh ASTM)
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-eae508a9ffc14ede9bea75e958bd22a6
Source dataset
uspto-grants-1984_10
Patent number
US04477662

Linked notes

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