Water → t-Butyl N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]-N-(2-hydroxyethyl)carbamate

HRID 748799Notes

Reaction equation

HRID 748799 reaction equation
[Si]([O:18][CH2:19][CH2:20][N:21]([CH2:29][CH2:30][CH:31]([S:40]([C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=1)(=[O:42])=[O:41])[C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[F:39])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[Cl:49][C:46]1[CH:45]=[CH:44][C:43]([S:40]([CH:31]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])[CH2:30][CH2:29][N:21]([CH2:20][CH2:19][OH:18])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:42])=[O:41])=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 59028248t-Butyl N-[2-(t-Butyldiphenylsilyloxy)ethyl]-N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]carbamate

Product 1

HCID 59750811t-Butyl N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]-N-(2-hydroxyethyl)carbamateYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (20 ml) was dissolved t-butyl N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]carbamate (1.13 g, 1.55 mmol). Under ice cooling, a tetrahydrofuran solution (1.0M, 5.0 ml, 5.0 mmol) of tetrabutylammonium fluoride was added dropwise. The resulting mixture was stirred at room temperature for 1 hour. Water (2 ml) was added to the reaction mixture. The residue obtained by concentrating the resulting mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated under reduced pressure, whereby the title compound (651 mg, 1.32 mmol, 85%) was obtained as a white foam.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the resulting mixture under reduced pressure
  3. customthe fraction obtained from the hexane

Sources & evidence

ORD record
ord-abca8a89d1924c268d94eeafb02dc829
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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