Methanol → 2-[2-(1-Benzyloxycarbonyl-piperidin-4-yl)-2-carboxy-ethanesulfonyl]-1,2,3,4-tetrahydro-beta-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl ester

HRID 1582041Notes

Reaction equation

HRID 1582041 reaction equation
[Cl:1][C:2]([Cl:49])([Cl:48])[CH2:3][O:4][C:5]([N:7]1[C:19]2[CH2:18][N:17]([S:20]([CH2:23][CH:24]([CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:39])[CH2:34][CH2:33]3)[C:25]([O:27]C(C)(C)C)=[O:26])(=[O:22])=[O:21])[CH2:16][CH2:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].CO>ClCCl>[Cl:49][C:2]([Cl:1])([Cl:48])[CH2:3][O:4][C:5]([N:7]1[C:19]2[CH2:18][N:17]([S:20]([CH2:23][CH:24]([CH:32]3[CH2:33][CH2:34][N:35]([C:38]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:39])[CH2:36][CH2:37]3)[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])[CH2:16][CH2:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 698964082-[2-(1-Benzyloxycarbonyl-piperidin-4-yl)-2-tert butoxy carbonyl-ethanesulfonyl]-1,2,3,4-tetrahydro-beta-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 101689782-[2-(1-Benzyloxycarbonyl-piperidin-4-yl)-2-carboxy-ethanesulfonyl]-1,2,3,4-tetrahydro-beta-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl esterYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from 2-[2-(1-benzyloxycarbonyl-piperidin-4-yl)-2-tert butoxy carbonyl-ethanesulfonyl]-1,2,3,4-tetrahydro-β-carboline-9-carboxylic acid 2,2,2-trichloro-ethyl ester (600 mg) to give, after chromatography (SiO2, 2.5% methanol in dichloromethane), the title compound (530 mg, 94%) as a pale yellow solid.

Workup

  1. customto give

Sources & evidence

ORD record
ord-142242485db64ff78725dfa2bd4efa11
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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