Water → HCID 54362405, compound

HRID 2081742Notes

Reaction equation

HRID 2081742 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]2[C@@H:3]1[S:4][C@@:5]([N:26]1[CH2:30][CH2:29][N:28]([N:31]=[CH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]1=[O:39])([C:10]([O:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:6]2.[CH3:40][O:41][C:42]1[CH:60]=[CH:59][C:45]([CH2:46][O:47][C:48](SC2N=C(C)C=C(C)N=2)=[O:49])=[CH:44][CH:43]=1.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH:32](=[N:31][N:28]1[CH2:29][CH2:30][N:26]([C@@:5]2([C:10]([O:12][CH:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:11])[S:4][C@H:3]3[N:7]([C:8](=[O:9])[C@H:2]3[NH:1][C:48]([O:47][CH2:46][C:45]3[CH:59]=[CH:60][C:42]([O:41][CH3:40])=[CH:43][CH:44]=3)=[O:49])[CH2:6]2)[C:27]1=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 100623S-(4,6-Dimethylpyrimidin-2-yl) O-(p-methoxybenzyl) thiocarbonateHCID 516892Sodium BicarbonateHCID 53864128HCID 53864128, compound

Product 1

HCID 54362405HCID 54362405, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 80 ml of methylene chloride was dissolved 7.50 g of (3R,5R,6R)-6-amino-3-(3-benzylideneamino-2-oxoimidazoldin-1-yl)-3-diphenylmethyloxycarbonyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane. Thereto was added 5 g of S-p-methoxybenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine. The mixture was stirred at room temperature for 2 hours. The reaction mixture was mixed with 80 ml of water, and the resulting mixture was adjusted to pH 7.0 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: chloroform/acetone=1/0 to 25/1) to obtain 8.36 g (yield: 85.2%) of (3R,5R,6R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-3-diphenylmethyloxycarbonyl-6-(p-methoxybenzyloxycarbonylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: chloroform/acetone=1/0 to 25/1)

Sources & evidence

ORD record
ord-fc0f57ebbbb646578d8f7ca620058eb3
Source dataset
uspto-grants-1993_02
Patent number
US05185330

Reaction notes

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