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

HRID 1632875

Reaction equation

HRID 1632875 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(C2N=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].[C:46]([NH:49][CH2:50][CH2:51][SH:52])(=[O:48])[CH3:47].O.[OH-].[Na+]>ClCCl.[Cl-].C([N+](C)(C)CCCCCCCCCCCCCCCC)C1C=CC=CC=1>[C:46]([NH:49][CH2:50][CH2:51][S:52][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:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:45][CH:44]=2)=[O:11])[CH3:14])[C:19]=1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)=[O:24])(=[O:48])[CH3:47]

Participants

7

Reactant 4

HCID 962WaterHCID 14484AcetylcysteamineHCID 14798Sodium HydroxideHCID 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 131713936p-Nitrobenzyl (5RS,6SR)-3-(2-acetamidoethylthio)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 31202Benzylhexadecyldimethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

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 (15 mg) in dichloromethane (2 ml) was cooled in an ice-bath and treated with benzyldimethyl-n-hexadecylammonium chloride (1.1 mg), followed by 2-acetamidoethanethiol (3 mg) in dichloromethane (1 ml), followed by water (1 ml), followed by 0.1M aqueous NaOH (0.25 ml). After stirring in the cold for 30 min. the reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. After dilution with CH2Cl2 /H2O and separation, the dichloromethane layer was dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with ethyl acetate, followed by ethylacetate/ethanol (95:5) to give the title compound νmax. (CH2Cl2) 3450, 1790, 1750, 1700(sh), 1680, 1525, 1350 cm-1.

Workup

  1. stirringstirred for 1.5 h
  2. customAfter dilution with CH2Cl2 /H2O and separation
  3. dry with materialthe dichloromethane layer was dried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d5695a4712ae4600a10a132b09ae61bf
Source dataset
uspto-grants-1984_10
Patent number
US04477662

Linked notes

Loading…