Water → (+/-)-Acetic acid (2RS,4aRS,10bRS)-6-(4-butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl ester

HRID 1867464

Reaction equation

P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][CH:24]([O:27][C:28](=[O:30])[CH3:29])[CH2:23][CH:22]2[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)=O)=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C.O>ClCCl>[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[CH:22]3[CH:21]([CH2:26][CH2:25][CH:24]([O:27][C:28](=[O:30])[CH3:29])[CH2:23]3)[N:20]=2)=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

1670 mg of phosphorous pentachloride are suspended in 2.5 ml of dichloromethane. 1119 mg of (±)-acetic acid (1RS,3RS,4RS)-4-{[1-(4-butoxy-phenyl)-methanoyl]-amino}-3-(3,4-dimethoxyphenyl)-cyclohexyl ester (compound A7) dissolved in 15 ml of dichloromethane are added and the mixture stirred for 18 h. The mixture is cooled to 0° C. and 10 ml of triethylamine added, then 5 ml of water. After phase separation and removal of solvent the solid residue is purified by flash chromatography [silica, toluene/dioxane=2:1 (containing 0.5% of ammonia)] to give 940 mg of the title compound as a colorless foam (87% of theory).

Workup

additionare added
customAfter phase separation and removal of solvent the solid residue
customis purified by flash chromatography [silica, toluene/dioxane=2:1 (containing 0.5% of ammonia)]

Sources & evidence

ORD record: ord-37d2ba67003e439c8dbfa5960c919ba3
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632844B2

Linked notes

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