Water → Acetic acid (2RS,4aRS,10bRS)-6-(2,6-dimethoxy-pyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-yl ester

HRID 334342Notes

Reaction equation

HRID 334342 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][O:8][C:9]1[C:14]([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:27])[CH3:26])[CH2:20][CH:19]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH2:37][CH3:38])[CH:29]=2)=O)=[CH:13][CH:12]=[C:11]([O:39][CH3:40])[N:10]=1.C(N(CC)CC)C.O>ClCCl>[CH3:7][O:8][C:9]1[C:14]([C:15]2[C:33]3[C:28](=[CH:29][C:30]([O:36][CH2:37][CH3:38])=[C:31]([O:34][CH3:35])[CH:32]=3)[CH:19]3[CH:18]([CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:27])[CH3:26])[CH2:20]3)[N:17]=2)=[CH:13][CH:12]=[C:11]([O:39][CH3:40])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 67022608acetic acid (1RS,3RS,4RS)-4-{[1-(2,6-dimethoxy-pyridin-3-yl)methanoyl]amino}-3-(3-ethoxy-4-methoxyphenyl)cyclohexyl ester2×

Product 1

HCID 67023839Acetic acid (2RS,4aRS,10bRS)-6-(2,6-dimethoxy-pyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-yl esterYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.67 g of phosphorus pentachloride are suspended in 5 ml of dichloromethane. 1.227 g of crude acetic acid (1RS,3RS,4RS)-4-{[1-(2,6-dimethoxy-pyridin-3-yl)methanoyl]amino}-3-(3-ethoxy-4-methoxyphenyl)cyclohexyl ester (compound A1) dissolved in 15 ml of dichloromethane are added and the reaction mixture stirred at room temperature over night. The reaction mixture is cooled with an ice bath and 20 ml of triethylamine are added, than cautiously 10 ml of water with vigorous stirring. The organic layer is separated, concentrated and the crude product purified by flash chromatography to give 715 mg of the title compound.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is cooled with an ice bath
  3. customThe organic layer is separated
  4. concentrationconcentrated
  5. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-e7e3df48586f4e099ed19c7726db7d6c
Source dataset
uspto-grants-2014_11
Patent number
US08883818B2

Reaction notes

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