Water → HCID 86746904, compound

HRID 1587147Notes

Reaction equation

HRID 1587147 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[C:29](O)(=[O:33])[C@H:30]([CH3:32])[OH:31].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[OH:31][C@@H:30]([CH3:32])[C:29]([O:19][C@H:18]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:17]1)=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 5997CholesterolHCID 6101p-Toluenesulfonic acidHCID 107689L-Lactic Acid

Product 1

HCID 86746904HCID 86746904, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.86 g of cholesterol and 0.85 ml of L-(+)-lactic acid (90% in water) in 80 ml of toluene is boiled for 1 hour. The water is separated, the cooled reaction mixture is treated with 0.3 g of p-toluene-sulphonic acid and boiled for a further 4 hours. The reaction mixture is treated with 30 ml of water and extracted with ether. The organic phase is dried over sodium sulphate and concentrated. The residue is purified on silica gel, with petroleum ether/ether 4:1 used as the elution agent. There are obtained 1.5 g of cholest-5-en-3β-yl (S)-2-hydroxypropionate, m.p. 120°-122° C.

Workup

  1. customThe water is separated
  2. customthe cooled reaction mixture
  3. extractionextracted with ether
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified on silica gel, with petroleum ether/ether 4:1

Sources & evidence

ORD record
ord-93f320b5653e47ab85645216f8ef4a2d
Source dataset
uspto-grants-1993_06
Patent number
US05215972

Reaction notes

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