Water → (+)-8-Chloro-6-methanesulfonyloxy-octanoic acid

HRID 2982Notes

Reaction equation

HRID 2982 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([OH:12])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH:4]([O:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 109544588-Chloro-6-hydroxyoctanoic acid

Product 1

HCID 18457707(+)-8-Chloro-6-methanesulfonyloxy-octanoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The methyl ester of (-)-8-chloro-6-hydroxy-octanoic acid (-)-(VIII), (R=Me) (2.1 g, 10 mmoles) and 1.0 g (10 mmoles) of triethylamine were mixed in 40 ml of toluene. While cooling to an internal temperature of 10° to 15° C., 1.4 g (12 mmoles) of methanesulfonyl chloride were added slowly. Stirring was continued for 30 minutes. After the addition of 25 ml of water, stirring was continued for a further 30 minutes, after which the organic phase was removed and dried over magnesium sulfate. The solvent was then evaporated under vacuum. The methyl ester of (-)-8-chloro-6-methanesulfonyloxy-octanoic acid (-)-(II), (R=R'=Me) was obtained in a yield of 2.5 g (88% of the theoretical yield). [α]D20 =-31.3 (c=1; ethanol).

Workup

  1. additionwere added slowly
  2. stirringstirring
  3. waitwas continued for a further 30 minutes
  4. customafter which the organic phase was removed
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was then evaporated under vacuum

Sources & evidence

ORD record
ord-4b0a7372fca44f93a027eca27e6da381
Source dataset
uspto-grants-1998_03
Patent number
US05731448

Reaction notes

Loading…