Methanol → HCID 131723093, compound

HRID 1250391Notes

Reaction equation

HRID 1250391 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]([C:12]2[N:13]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36](=S)[NH2:37])[CH:31]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:16][CH:15]=3)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[C:41]([O-:44])(=[O:43])[CH3:42].[NH4+:45].CO>CC(C)=O>[C:41]([OH:44])(=[O:43])[CH3:42].[C:1]1([C@H:7]([NH:9][C:10]([C:12]2[N:13]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36](=[NH:37])[NH2:45])[CH:31]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:16][CH:15]=3)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 54048509HCID 54048509, compound

Product 1

HCID 131723093HCID 131723093, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

This compound was prepared from (R)-5-benzyloxy-1-(3-thiocarbamoyl-benzyl)-1H-indole-2-carboxylic acid (1-phenyl-ethyl)-amide, methyl iodide, and ammonium acetate as described in example 1/5, but for the methylation acetone was used as solvent and in the last step methanol and acetone were used as solvents. The crude material was purified by flash chromatography on silica gel with dichloromethane/methanol/acetic acid 9:0.25:0.5 to give the desired product in 28% yield. M.p. 72° C. (dec.). MS: 503.3 (M+H+).

Workup

  1. customThe crude material was purified by flash chromatography on silica gel with dichloromethane/methanol/acetic acid 9:0.25:0.5

Sources & evidence

ORD record
ord-ad5dc445e30e4f298bde2d20de77e20f
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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