Ethyl Acetate → HCID 58972207, compound

HRID 2076793Notes

Reaction equation

HRID 2076793 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C@@:8]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][Si](C(C)(C)C)(C)C)=[CH:17][CH:16]=1)([CH3:12])[C@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O.C([O-])(O)=O.[Na+]>C(#N)C>[C:1]([O:5][C:6](=[O:29])[NH:7][C@@:8]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([CH3:12])[C@H:9]([OH:11])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 67100017HCID 67100017, compound

Product 1

HCID 58972207HCID 58972207, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of ((1R,2R)-1-{2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-ethyl}-2-hydroxy-1-methyl-propyl)-carbamic acid tert-butyl ester (19 mg, 0.045 mMol) in acetonitril (2 ml) is added HF (0.2 ml, 40% solution), and the reaction is stirred at RT for 3.5 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 30% AcOEt in heptane gives the title compound.

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 30% AcOEt in heptane

Sources & evidence

ORD record
ord-77df8bfeed0b42e99fe3c7b97e4d35ce
Source dataset
uspto-grants-2011_04
Patent number
US07928093B2

Reaction notes

Loading…