Ethyl Acetate → HCID 14156318, compound

HRID 1710176Notes

Reaction equation

HRID 1710176 reaction equation
Cl.[C:2]([O:5][C@@H:6]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:11][C:10]2[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=[CH:24][C:9]=2[N:8]([CH2:29][CH2:30][NH:31][CH3:32])[C:7]1=[O:33])(=[O:4])[CH3:3].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O>[C:2]([O:5][C@@H:6]1[C@H:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:11][C:10]2[C:21]([C:25]([F:27])([F:28])[F:26])=[CH:22][CH:23]=[CH:24][C:9]=2[N:8]([CH2:29][CH2:30][NH:31][CH3:32])[C:7]1=[O:33])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131716526HCID 131716526, compound

Product 1

HCID 14156318HCID 14156318, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3.0 g of (3R-cis)-3-(acetyloxy)-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-1-[2-(methylamino) ethyl]-6-(trifluoromethyl)-2H-1-benzazepin-2-one, monohydrochloride, prepared as described in U.S. Pat. No. 4,748,239, Example 43, in 15 ml of water was treated with 75 ml of ethyl acetate, followed by the portionwise addition of a solution of 1.3 g of sodium hydrogen carbonate in 10 ml of water. The mixture was shaken and the sl. alkaline aqueous phase was discarded. The organic phase was extracted with 10 ml of water (2×) and then with 10 ml of saturated sodium chloride solution, dried over magnesium sulfate, filtered thorugh a celite bed, and the colorless filtrate was concentrated on a rotary evaporator to give 2.32 g of a colorless solid. The latter was suspended in 15 ml of hexane and filtered to give 2.19 g (90%) of the title A compound as a colorless solid, m.p. 140°-143° C.

Workup

  1. extractionThe organic phase was extracted with 10 ml of water (2×)
  2. dry with materialwith 10 ml of saturated sodium chloride solution, dried over magnesium sulfate
  3. filtrationfiltered thorugh a celite bed
  4. concentrationthe colorless filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-cd8a9f0aed954ea0902dbf03153f78de
Source dataset
uspto-grants-1990_08
Patent number
US04952692

Reaction notes

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