Water → HCID 58972204, compound

HRID 2076792Notes

Reaction equation

HRID 2076792 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@:8]([C:26](C)(C)[O:27][SiH2]C(C)(C)C)([CH3:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].O.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(#N)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[C:1]([O:5][C:6](=[O:35])[NH:7][C@:8]([CH2:26][OH:27])([CH3:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131728784HCID 131728784, compound

Product 1

HCID 58972204HCID 58972204, compound

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of {(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-methyl-propyl}-carbamic acid tert-butyl ester (8.84 g, 16.8 mMol) in acetonitrile (150 ml) is added H2O (1.52 ml, 84.3 mMol) and Sc(OTf)3 (83 mg, 0.2 mMol). The reaction is stirred at RT for 3 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted with AcOEt (3 times). The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 0%→40% AcOEt in heptane gives {(R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-hydroxymethyl-1-methyl-propyl}-carbamic acid tert-butyl ester as a colourless oil.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt (3 times)
  2. dry with materialThe combined organic layers are dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. washColumn chromatography eluting with 0%→40% AcOEt in heptane

Sources & evidence

ORD record
ord-c94b2916c0f84965bf056e4a1dc872a0
Source dataset
uspto-grants-2011_04
Patent number
US07928093B2

Reaction notes

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