Water → 3-Methanesulphonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

HRID 37014Notes

Reaction equation

HRID 37014 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7](=[N:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH3:8])[CH2:3]1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:23][S:24]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7](=[N:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH3:8])[CH2:3]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 541832563-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

Product 1

HCID 539971713-Methanesulphonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 32.2 g of 3-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine in 500 ml of methylene chloride, were added, with ice-cooling, 9.3 ml of methanesulphonyl chloride, followed by 16.7 ml of triethylamine. The mixture was stirred for 30 minutes, with ice-cooling, and then water was added, after which the mixture was extracted with methylene chloride and the extract was washed with water and dried, to give 36 g of the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionafter which the mixture was extracted with methylene chloride
  4. washthe extract was washed with water
  5. customdried

Sources & evidence

ORD record
ord-990140d1b6794a5dba00262ab945cfb6
Source dataset
uspto-grants-1995_05
Patent number
USRE034960

Reaction notes

Loading…