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

HRID 2981Notes

Reaction equation

HRID 2981 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) (4.0 g, 19.2 mmoles) and 1.97 g (19.2 mmoles) of triethylamine were mixed in 90 ml toluene. While cooling to an internal temperature of 10° to 15° C., 2.63 g (23.0 mmoles) of methanesulfonyl chloride were added slowly. Stirring was continued for 30 minutes. After the addition of 30 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 4.8 g (88% of the theoretical yield). [α]D20 =+31.2° (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-1c03739439424e59810e1f608eed556f
Source dataset
uspto-grants-1998_03
Patent number
US05731448

Reaction notes

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