Methanol → HCID 86586125, compound

HRID 751458Notes

Reaction equation

HRID 751458 reaction equation
[OH:1][CH:2]1[CH:8]([NH:9][C:10]([C@@H:12]([NH:17][C:18]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[CH:24]=2)=[O:19])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([S:42](Cl)(=[O:44])=[O:43])[CH:37]=1.CO>ClCCl.C(OCC)(=O)C>[CH3:16][CH:14]([CH3:15])[CH2:13][C@H:12]([NH:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[CH:24]=1)=[O:19])[C:10](=[O:11])[NH:9][CH:8]1[CH2:7][CH2:6][CH2:5][N:4]([S:42]([C:38]2[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=2)(=[O:44])=[O:43])[CH2:3][CH:2]1[OH:1]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 86586124HCID 86586124, compound

Product 1

HCID 86586125HCID 86586125, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzofuran-2-carboxylic acid [(S)-1-(3-hydroxy-azepan-4-ylcarbamoyl)-3-methyl-butyl]-amide of Example 78c (0.3 g) in dichloromethane was added triethylamine (0.17 mL) followed by 3-pyridinesulfonyl chloride (0.25 g). The reaction was stirred at room temperature until complete as determined by TLC analysis. Workup and column chromatography (5% methanol:ethyl acetate) provided 0.32 g of the title compound: MS(EI) 528 (M+H+).

Sources & evidence

ORD record
ord-d847297ee4274afbae916408fa2673fd
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

Loading…