Cinchonine → Cinchonine

HRID 274077

Reaction equation

HRID 274077 reaction equation
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[CH2:20]=[CH:21][C@@H:22]1[C@@H:27]2[CH2:28][C@H:29]([C@@H:30]([OH:41])[C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=[CH:33][CH:32]=3)[N:24]([CH2:25][CH2:26]2)[CH2:23]1>O1CCOCC1>[C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[CH2:20]=[CH:21][C@@H:22]1[C@@H:27]2[CH2:28][C@H:29]([C@@H:30]([OH:41])[C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=[CH:33][CH:32]=3)[N:24]([CH2:25][CH2:26]2)[CH2:23]1

Participants

5

Reactant 2

HCID 90454CinchonineHCID 20094784HCID 20094784, compound

Product 2

HCID 90454CinchonineYield 106.4%HCID 54405639HCID 54405639, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-acetylamino-5-(3-methoxyphenyl)valeric acid (151 mg) and (+)-cinchonine (110 mg) in 1,4-dioxane (2.6 ml) was refluxed and the solution was allowed to cool. The resulting precipitates were collected by filtration and dried to give a salt of (S)-4-acetylamino-5-(3-methoxyphenyl)valeric acid and (+)-cinchonin (117 mg). This compound was recrystallized from 1,4-dioxane to give the pure salt (61 mg).

Workup

  1. temperaturewas refluxed
  2. temperatureto cool
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-1c230b43ee81457ea588668951a8d813
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Linked notes

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