Boron trifluoride etherate → 1-[(4'-Fluorobiphenyl-4-sulfonyl)-(3-hydroxypropyl)amino]-cyclopentanecarboxylic acid benzyl ester

HRID 1872220Notes

Reaction equation

HRID 1872220 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:33][CH2:34][CH2:35][O:36][Si](C(C)(C)C)(C)C)[S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1([N:16]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:33][CH2:34][CH2:35][OH:36])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 154800091-[[3-(Tert-butyl-dimethylsilanyloxy)propyl)-(4'-fluorobiphenyl-4-sulfonyl)amino]-cyclopentanecarboxylic acid benzyl ester

Product 1

HCID 154800101-[(4'-Fluorobiphenyl-4-sulfonyl)-(3-hydroxypropyl)amino]-cyclopentanecarboxylic acid benzyl esterYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude 1-[[3-(tert-butyl-dimethylsilanyloxy)propyl]-(4'-fluorobiphenyl-4-sulfonyl)amino]cyclopentanecarboxylic acid benzyl ester (27.35 grams) in methylene chloride (450 mL) at room temperature was added boron trifluoride etherate (11 mL, 89.4 mmol). After 45 minutes, the reaction was quenched by sequential addition of saturated ammonium chloride solution and water. The organic phase was separated, washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent under vacuum provided crude 1-[(4'-fluorobiphenyl-4-sulfonyl)-(3-hydroxypropyl)amino]cyclopentane carboxylic acid benzyl ester as an amber oil (22.1 grams).

Workup

  1. customthe reaction was quenched by sequential addition of saturated ammonium chloride solution and water
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-acee0fc27c274ca08d67e7c454d0f46d
Source dataset
uspto-grants-2000_08
Patent number
US06107337

Reaction notes

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