Citric Acid → HCID 10394323, compound

HRID 2357488Notes

Reaction equation

HRID 2357488 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:14]2)=[O:12])[CH2:5][CH2:4]1.C(O)C.[C:37]([OH:49])(=[O:48])[CH2:38][C:39]([CH2:44][C:45]([OH:47])=[O:46])([C:41]([OH:43])=[O:42])[OH:40]>C(OCC)C>[C:37]([OH:49])(=[O:48])[CH2:38][C:39]([CH2:44][C:45]([OH:47])=[O:46])([C:41]([OH:43])=[O:42])[OH:40].[CH3:1][N:2]([CH3:33])[C:3]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:14]2)=[O:12])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 702EthanolHCID 10394324HCID 10394324, compound

Product 1

HCID 10394323HCID 10394323, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The polar diastereoisomer of 3-(1H-indol-3-yl)pyrrolidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexyl-methyl)-amide (115 mg, 0.241 mmole) was dissolved in abs. ethanol (1.5 ml). Citric acid (46.8 mg, 0.244 mmole) was added in one portion at ca. 40° C. while stirring. No precipitate formed at RT. The amount of solvent was reduced to 2 ml in vacuo and diethyl ether (20 ml) was then added. After stirring overnight at RT the precipitate was filtered off, washed with diethyl ether (3×3 ml) and dried in vacuo. The non-polar diastereoisomer of 3-(1H-indol-3-yl)pyrrolidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide citrate (312 mg, 94%, Example 52) was a pale beige solid.

Workup

  1. customNo precipitate formed at RT
  2. additionwas then added
  3. stirringAfter stirring overnight at RT the precipitate
  4. filtrationwas filtered off
  5. washwashed with diethyl ether (3×3 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0bac0a96732f46b3b33e24466b1958ab
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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