Citric Acid → HCID 10009809, compound

HRID 1394283Notes

Reaction equation

HRID 1394283 reaction equation
[C:1]([O-:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([O-:11])=[O:10])([C:5]([O-:7])=[O:6])[OH:4].[CH3:14][O:15][C:16](=[O:48])[CH:17]([NH:28][C:29]([NH:31][CH2:32][CH:33]1[CH2:38][CH2:37][C:36]([N:45]([CH3:47])[CH3:46])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:35][CH2:34]1)=[S:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH3:14][O:15][C:16](=[O:48])[CH:17]([NH:28][C:29]([NH:31][CH2:32][CH:33]1[CH2:38][CH2:37][C:36]([N:45]([CH3:46])[CH3:47])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:35][CH2:34]1)=[S:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31348CitrateHCID 10009810HCID 10009810, compound

Product 1

HCID 10009809HCID 10009809, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In order to produce the citrate, the more nonpolar diastereoisomer of 2-[3-(4-dimethylamino-4-phenylcyclohexylmethyl)thioureido]-3-(1H-indol-3-yl)propionic acid methyl ester (135 mg, 0.274 mmole) was dissolved in hot ethanol (11 ml) and combined with a solution of citric acid (57.9 mg, 0.3 mmole) in ethanol (1 ml). After 4 h, no precipitate was visible. Ethanol was removed by distillation down to a volume of 2 ml and the mixture was slowly combined with ether (30 ml). The suspension was stirred for 20 h at RT and cooled for 2 h in the refrigerator. The resultant solid was filtered out, washed with cold ether (2×1 ml) and dried. The nonpolar diastereoisomer of 2-[3-(4-dimethylamino-4-phenylcyclohexylmethyl)thioureido]-3-(1H-indol-3-yl)propionic acid methyl ester citrate could be obtained in this manner as a yellow solid (Example 41, m.p. 158-163° C.) in a yield of 165 mg (88%).

Workup

  1. customEthanol was removed by distillation down to a volume of 2 ml
  2. temperaturecooled for 2 h in the refrigerator
  3. filtrationThe resultant solid was filtered out
  4. washwashed with cold ether (2×1 ml)
  5. customdried

Sources & evidence

ORD record
ord-ccf90df511e2434fa5e5571755859277
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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