Dibutyltin dichloride → 3-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-thiophene-2-carboxylic acid methyl ester

HRID 579186Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:11]([O:13][C:14](=[O:26])[CH2:15][CH2:16][CH2:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=O)[CH3:12].C1([SiH3])C=CC=CC=1.C([Sn](Cl)(Cl)CCCC)CCC>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:17][CH2:16][CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:26])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A flask was charged with 3-amino-thiophene-2-carboxylic acid methyl ester (600 mg, 3.82 mmol, 1.0 equiv), 5-cyclohexyl-5-oxo-pentanoic acid ethyl ester (864 mg, 3.82 mmol, 1.0 equiv), phenyl silane (496 mg, 4.58 mmol, 1.2 equiv), dibutyltin dichloride (116 mg, 0.38 mmol, 0.1 equiv) and dioxane (3.0 mL). The resulting solution was heated at 60° C. for 18 hours. The solution was then concentrated and the residue was purified by silica gel column chromatography, CH2Cl2/heptane 30% to 100%, to give 3-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-thiophene-2-carboxylic acid methyl ester 810 mg (yield 57%).

Workup

concentrationThe solution was then concentrated
customthe residue was purified by silica gel column chromatography, CH2Cl2/heptane 30% to 100%

Sources & evidence

ORD record: ord-914684d1c8fa49dbb645010e8de4bd36
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040690B2

Reaction notes

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