(-)-Dihydroquinine → (2S,3S)-2-(2-benzyloxyphenyl)-3-cyclohexyl-3-hydroxypropionic acid

HRID 1533263Notes

Reaction equation

HRID 1533263 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([CH:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[OH:20])[C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][CH2:28][C@@H:29]1[C@@H:34]2[CH2:35][C@@H:36]([C@H:37]([OH:50])[C:38]3[CH:47]=[CH:46][N:45]=[C:44]4[C:39]=3[CH:40]=[C:41]([O:48][CH3:49])[CH:42]=[CH:43]4)[N:31]([CH2:32][CH2:33]2)[CH2:30]1>ClCCl>[CH3:27][CH2:28][C@@H:29]1[C@@H:34]2[CH2:35][C@@H:36]([C@H:37]([OH:50])[C:38]3[CH:47]=[CH:46][N:45]=[C:44]4[C:39]=3[CH:40]=[C:41]([O:48][CH3:49])[CH:42]=[CH:43]4)[N:31]([CH2:32][CH2:33]2)[CH2:30]1.[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C@@H:15]([C@H:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[OH:20])[C:16]([OH:18])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 121515(-)-DihydroquinineHCID 22012324HCID 22012324, compound

Product 2

HCID 121515(-)-DihydroquinineHCID 57219069(2S,3S)-2-(2-benzyloxyphenyl)-3-cyclohexyl-3-hydroxypropionic acidYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2RS,3RS)-2-(2-benzyloxyphenyl)-3-cyclohexyl-3-hydroxypropionic acid (354 mg) in dichloromethane (7 ml) was added hydroquinine (326 mg) and the mixture was stirred to be a clear solution. The solvent was evaporated under reduced pressure and the residue was crystallized from ethyl acetate. Precipitates were recrystallized from a mixture of ethyl acetate and ethanol (50:1) to afford hydroquinine salt of (2S,3S)-2-(2-benzyloxyphenyl)-3-cyclohexyl-3-hydroxypropionic acid as crystals (150 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was crystallized from ethyl acetate
  3. customPrecipitates
  4. customwere recrystallized from a mixture of ethyl acetate and ethanol (50:1)

Sources & evidence

ORD record
ord-404c87f535204e1cb12ebf7d5d5ee960
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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