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Hydrofluoric Acid → (5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid methyl ester

HRID 1819942
Notes
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Reaction equation

HRID 1819942 reaction equation
[CH3:1][O:2][C:3](=[O:5])[CH3:4].C([Si](C)(C)[O:11][CH:12]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:26]2[S:30][C:29]([S:31]([NH2:34])(=[O:33])=[O:32])=[C:28]([CH3:35])[CH:27]=2)([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:17][C:16]=1[CH3:36])(C)(C)C.F>C(#N)C>[CH3:1][O:2][C:3](=[O:5])[CH3:4].[CH2:22]([C:21]([C:26]1[S:30][C:29]([S:31]([NH2:34])(=[O:33])=[O:32])=[C:28]([CH3:35])[CH:27]=1)([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH:12]([OH:11])[C:37]([CH3:39])([CH3:40])[CH3:38])=[C:16]([CH3:36])[CH:17]=1)[CH2:24][CH3:25])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 68625648[5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonylamine]-acetic acid methyl ester

Product 1

HCID 68625699(5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a solution of [5-(1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonylamine]-acetic acid methyl ester (380 mg, 0.59 mmol) in acetonitrile (10 ml) at 0° C. is added hydrofluoride solution (3 ml, 48% in water). After stirring at RT for 2 h, the reaction is concentrated and partitioned between EtOAc and 1N HCl. The organic layer is washed successively with 1N HCl and brine. Tle organic layer is concentrated and chromatographed (Hex to 25% EtOAc/Hex) to give the title compound (250 mg, 82%).

Workup

  1. concentrationthe reaction is concentrated
  2. custompartitioned between EtOAc and 1N HCl
  3. washThe organic layer is washed successively with 1N HCl and brine
  4. concentrationTle organic layer is concentrated
  5. customchromatographed (Hex to 25% EtOAc/Hex)

Sources & evidence

ORD record
ord-ed443022bc5d4143b65727236f1fca25
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601850B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes