Boron trifluoride etherate → HCID 54387880, compound

HRID 1859355Notes

Reaction equation

HRID 1859355 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[CH:10]([N:17]([CH2:29][CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[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](=[O:40])[CH:10]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[N:17]([CH2:29][CH2:30][CH2:31][OH:32])[S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 54014866HCID 54014866, compound

Product 1

HCID 54387880HCID 54387880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [[3-(tert-butyldimethylsilanyloxy)propyl](4-methoxybenzenesulfonyl) amino]cyclohexylacetic acid benzyl ester (13.67 grams, 23.2 mmol) in methylene chloride (60 mL) at room temperature was added boron trifluoride etherate (21 mL, 171 mmol). After 20 minutes, the reaction was quenched by addition of saturated ammonium chloride solution and subsequent addition of ethyl acetate and water. The organic phase was separated, washed with brine and dried over magnesium sulfate. Evaporation of the solvent under vacuum gave an oil from which cyclohexyl[(3-hydroxypropyl)(4-methoxy-benzenesulfonyl)amino]acetic acid benzyl ester, a clear oil (11.25 grams, 100%), was isolated by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane and then 40% ethyl acetate in hexane.

Workup

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

Sources & evidence

ORD record
ord-ae0d3f18b7cf4525959e57490e6d32f2
Source dataset
uspto-grants-2000_11
Patent number
US06153609

Reaction notes

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