Water → HCID 54362405, compound

HRID 1463442Notes

Reaction equation

HRID 1463442 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-oxoimidazolidin-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-9236803c568e4937825fb512d74f3019
Source dataset
uspto-grants-1994_04
Patent number
US05300497

Reaction notes

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