Diethyl Ether → (2S)-2-[2-(4-Dimethylamino-4-phenylcyclohexyl)acetylamino]-3-(1H-indol-3-yl)propanoic acid methyl ester hydrochloride

HRID 908969Notes

Reaction equation

HRID 908969 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:15][C:16](=[O:33])[CH2:17][CH:18]1[CH2:23][CH2:22][C:21]([N:30]([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[Cl:35][Si](C)(C)C.CCOCC>CC(CC)=O>[ClH:35].[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:15][C:16](=[O:33])[CH2:17][CH:18]1[CH2:19][CH2:20][C:21]([N:30]([CH3:31])[CH3:32])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:23]1)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 67386266(2S)-2-[2-(4-Dimethylamino-4-phenylcyclohexyl)acetylamino]-3-(1H-indol-3-yl)propanoic acid methyl ester

Product 1

HCID 67386274(2S)-2-[2-(4-Dimethylamino-4-phenylcyclohexyl)acetylamino]-3-(1H-indol-3-yl)propanoic acid methyl ester hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

(2S)-2-[2-(4-Dimethylamino-4-phenylcyclohexyl)acetylamino]-3-(1H-indol-3-yl)propanoic acid methyl ester (271 mg, 0.587 mmol) was dissolved in ethyl methyl ketone, and chlorotrimethylsilane (0.111 ml, 0.88 mmol) was added. After 1 h ether (30 ml) was added to the mixture and the mixture was stirred for a further 10 min. The hydrochloride was filtered off and obtained as a colourless solid in a yield of 96% (278 mg) with an m.p. of 239-241° C.

Workup

  1. filtrationThe hydrochloride was filtered off
  2. customobtained as a colourless solid in a yield of 96% (278 mg) with an m.p. of 239-241° C.

Sources & evidence

ORD record
ord-ca096800056a419e9498e922c8f5fbbd
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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