Pinoline → 2-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid tert-butyl ester

HRID 1582037Notes

Reaction equation

HRID 1582037 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH:7]([CH2:11][S:12](Cl)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]1[CH2:28][NH:29][CH2:30][CH2:31][C:22]2=1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6](=[O:16])[CH:7]([CH2:11][S:12]([N:29]1[CH2:30][CH2:31][C:22]2[C:21]3[C:25](=[CH:26][CH:27]=[C:19]([O:18][CH3:17])[CH:20]=3)[NH:24][C:23]=2[CH2:28]1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1868PinolineHCID 8471TriethylamineHCID 212590942-Chlorosulfonylmethyl-3-methyl-butyric acid tert-butyl ester

Product 1

HCID 698956642-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid tert-butyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chlorosulfonylmethyl-3-methylbutyric acid tert-butyl ester (WO 99/24399) (470 mg) in dichloromethane (10 ml) was added to a mixture of 6-methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (350 mg) and triethylamine (0.72 ml) in dichloromethane (10 ml) at room temperature under nitrogen. The mixture was stirred for 20 minutes before being evaporated to dryness and the residue chromatographed (SiO2, 1:1 heptane-ethyl acetate) to give the title compound (487 mg, 66%) as a white solid.

Workup

  1. custombefore being evaporated to dryness
  2. customthe residue chromatographed (SiO2, 1:1 heptane-ethyl acetate)

Sources & evidence

ORD record
ord-bc77e4e0dec9436faf508d28bd2f6eed
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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