Benzoyl chloride → HCID 71763880, compound

HRID 1644781Notes

Reaction equation

HRID 1644781 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][N:21]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]3)[C@@H:18]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:14][OH:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>N1C=CC=CC=1>[C:42]([O:15][CH2:14][C@H:13]([C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=1)[O:16][C@H:17]1[CH2:25][CH2:24][C@H:23]2[C@@H:19]([CH2:20][N:21]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]2)[C@@H:18]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39])(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 25028926HCID 25028926, compound

Product 1

HCID 71763880HCID 71763880, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the (1S) isomer of EXAMPLE 1 (tert-Butyl (3aR,4R,5S,7aS)-5-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy}-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate, 8.61 g, 14.65 mmol) in 50 mL pyridine was added benzoyl chloride (3.40 mL, 29.3 mmol). The mixture was stirred at 50° C. for 16 hr. The volatiles were removed in vacuo. The residue was dissolved in 200 mL ethyl acetate, washed with sodium bicarbonate aqueous and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexane, 15% to 30% for 2900 mL, then 30% to 50% for 1250 mL) to give 10.38 g (102% yield) of the title compound. M++1: 588.1.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in 200 mL ethyl acetate
  3. washwashed with sodium bicarbonate aqueous and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (EtOAc/hexane, 15% to 30% for 2900 mL

Sources & evidence

ORD record
ord-c213b04426ab493fa65c5a8e99996e1d
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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