Dichloromethane → HCID 70343329, compound

HRID 341904Notes

Reaction equation

HRID 341904 reaction equation
[CH2:1]([C@:8]1([C:21](=[O:23])[NH2:22])[C:14]([CH3:16])([CH3:15])[S@@:13](=[O:17])[C@H:12]2[N:9]1[C:10](=[O:20])[C:11]2(Br)[Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>O>[CH2:1]([C@:8]1([C:21](=[O:23])[NH2:22])[C:14]([CH3:16])([CH3:15])[S@:13](=[O:17])[C@H:12]2[N:9]1[C:10](=[O:20])[C@@H:11]2[Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 70343658HCID 70343658, compound

Product 1

HCID 70343329HCID 70343329, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold (0° C.) solution of (2S,4R,5R)-2-benzyl-carbamoyl-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-4-oxide (1160 mg, 2.5 mmole) in dry methylene chloride (30 ml) triphenyl phosphine (837 mg, 5 mmole) was added and it was stirred for 15 minutes. The reaction mixture was treated with water and the layers were separated. The organic layer was washed with water, then with a saturated sodium hydrogen carbonate solution and again with water. The evaporation of dry (Na2SO4) organic layer under reduced pressure gave a foamy residue, which after chromatography on silica gel gave (2S,4S,5R,6S)-2-benzyl-carbamoyl-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-4-oxide (780 mg, 81.0%). Crystallization from diethyl ether gave the product as a white crystalline powder.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water
  3. customThe evaporation
  4. dry with materialof dry (Na2SO4) organic layer under reduced pressure
  5. customgave a foamy residue, which after chromatography on silica gel

Sources & evidence

ORD record
ord-9a69c9167d614ac991270bf619417928
Source dataset
uspto-grants-1999_01
Patent number
US05856475

Reaction notes

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