Hydroquinone → HCID 13219901, compound

HRID 342294Notes

Reaction equation

HRID 342294 reaction equation
[N+:1]([C:4]1[CH:68]=[CH:67][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][S:15][C:16]([CH2:18][C@H:19]2[N:22]([C:23]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=[O:38])=P(OC(C)C)(OC(C)C)OC(C)C)[C:21](=[O:50])[C@@H:20]2[C@H:51]([O:53][C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[CH:60][CH:59]=2)=[O:55])[CH3:52])=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C=CC(O)=CC=1)O>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:68]=[CH:67][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][S:15][C:16]2[CH2:18][C@@H:19]3[C@@H:20]([C@H:51]([O:53][C:54]([O:56][CH2:57][C:58]4[CH:63]=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[CH:60][CH:59]=4)=[O:55])[CH3:52])[C:21](=[O:50])[N:22]3[C:23]=2[C:37]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=2)=[O:38])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 88672495HCID 88672495, compound

Product 1

HCID 13219901HCID 13219901, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 48 mg of (3S, 4R)-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonylmethyl)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-2-azetidinone and 30 mg of hydroquinone in 5 ml of xylene was heated at 120° C. under a stream of a nitrogen gas for 13 hours. The xylene was then distilled off and the residue was subjected to chromatography using a Lobar column A eluted with a 2:1 by volume mixture of chloroform and ethyl acetate, to give crude crystals, which were recrystallized from a mixture of benzene and ethyl acetate, affording 19 mg (yield 51%) of colourless prisms, melting at 148°-150° C.

Workup

  1. distillationThe xylene was then distilled off
  2. washA eluted with a 2:1 by volume mixture of chloroform and ethyl acetate
  3. customto give crude crystals, which
  4. customwere recrystallized from a mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-411d238bfa2f41eb8cc114bc92e7566b
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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