3,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester → 2-[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

HRID 992428Notes

Reaction equation

HRID 992428 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][S:19](Cl)(=[O:21])=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:30][C:31]([Cl:57])([Cl:56])[CH2:32][O:33][C:34]([N:36]1[C:48]2[CH2:47][N:46](C(OC(C)(C)C)=O)[CH2:45][CH2:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:35]>CCCCCCC.C(OCC)(=O)C>[Cl:57][C:31]([Cl:30])([Cl:56])[CH2:32][O:33][C:34]([N:36]1[C:48]2[CH2:47][N:46]([S:19]([CH2:18][CH:17]([CH:14]3[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12][CH2:13]3)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:21])=[O:20])[CH2:45][CH2:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:35]

Participants

4

Reactant 2

HCID 698941943,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) esterHCID 865842754-(1-Tert-butoxycarbonyl-2-chlorosulfonyl-ethyl)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 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 esterYield 71.9%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

Prepared from 4-(1-tert-butoxycarbonyl-2-chlorosulfonyl-ethyl)-piperidine-1-carboxylic acid benzyl ester (640 mg) and 3,4-dihydro-1H-β-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester (500 mg) to give, after chromatography (SiO2, 2:1 heptane-ethyl acetate), the title compound (608 mg, 61%) as a white solid.

Workup

  1. customto give

Sources & evidence

ORD record
ord-c9676327eda2488c8b0e6a8f20e5a440
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

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