Hydroquinone → HCID 56975877, compound

HRID 1029685Notes

Reaction equation

HRID 1029685 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17](=O)[CH2:18][C@H:19]2[N:22]([C:23](=O)[C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])[C:21](=[O:38])[C@@H:20]2[C@H:39]([O:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[CH3:40])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(OCC)(OCC)OCC.C1(C=CC(O)=CC=1)O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH2:18][C@H:19]3[N:22]([C:21](=[O:38])[C@@H:20]3[C@H:39]([O:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[CH3:40])[C:23]=2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 31215Triethyl phosphiteHCID 67837029HCID 67837029, compound

Product 1

HCID 56975877HCID 56975877, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-nitrobenzyl 2-[(3S,4R)-4-{2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl}-3-{(1R)-1-trimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-oxoacetate (4.73 g) and triethyl phosphite (6.2 ml) in toluene (70 ml) was heated under reflux for 2 hours under nitrogen atmosphere. To this solution was added hydroquinone (800 mg), and the reflux was continued for additional 6 hours. The solvent was removed in vacuo to give a residue, which was chromatographed on silica gel (400 ml) eluting with a mixture of hexane and ethyl acetate (4:1 v/v) to give 4-nitrobenzyl (5R,6S)-3-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-trimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (3.77 g).

Workup

  1. temperatureunder reflux for 2 hours under nitrogen atmosphere
  2. customThe solvent was removed in vacuo
  3. customto give a residue, which
  4. customwas chromatographed on silica gel (400 ml)
  5. washeluting with a mixture of hexane and ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-68e16652516848bfb5a0c9f63a35b7a7
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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