Water → Methyl 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1904459Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:31]([CH:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34](Cl)=[O:35])[CH3:32].O>C(Cl)Cl.C(OCC)(=O)C>[CH2:31]([CH:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][CH:3]=1)=[O:35])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of methyl ester (B) (0.5 g) in methylene chloride (16 ml) was cooled to 0° C. and treated with triethylamine (0.34 ml) followed by 2-ethylhexanoyl chloride (0.31 ml). The resulting solution was stirred at 0° C. for 15 minutes and then at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and poured into cold water. The organic layer was washed sequentially with 10% v/v hydrochloric acid, water, and brine; dried (MgSO4) and evaporated. The residue was purified by flash chromatography on a 4×18 cm silica gel column using 35:65 v/v ethyl acetate:hexane as the eluent to give methyl 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoate (C) (0.7 g; 99%) as a white solid; partial NMR: 0.9(t, 6H, 2CH3), 1.5(m, 9H).

Workup

waitat room temperature for 30 minutes
washThe organic layer was washed sequentially with 10% v/v hydrochloric acid, water, and brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by flash chromatography on a 4×18 cm silica gel column

Sources & evidence

ORD record: ord-cb4cecfb6362403db8992f1b99b82c05
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04837235

Reaction notes

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