Ethyl Acetate → HCID 86598939, compound

HRID 1244651Notes

Reaction equation

HRID 1244651 reaction equation
C(OC([CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([C@@H:23]([OH:32])[C@H:24]([O:29][CH2:30][CH3:31])[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.C([SiH](CC)CC)C.C(OCC)(=O)C.[OH-].[Na+]>FC(F)(F)C(O)=O>[CH2:30]([O:29][C@@H:24]([C@H:23]([OH:32])[C:20]1[CH:21]=[CH:22][C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][NH:9][CH3:8])[CH:12]=2)=[CH:18][CH:19]=1)[C:25]([O:27][CH3:28])=[O:26])[CH3:31]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 86598940HCID 86598940, compound

Product 1

HCID 86598939HCID 86598939, compoundYield 120.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

21 g (47.3 mmol) of methyl (2S,3R)-3-{3′-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxy-3-hydroxypropionate, 8.76 ml (54.9 mmol) of triethylsilane in 300 ml of trifluoroacetic acid are introduced into a round-bottomed flask and under a nitrogen stream. The reaction medium is stirred for 4 hours at room temperature. Ethyl acetate is then added and the mixture is neutralized with sodium hydroxide. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and evaporated off. 19.6 g (100%) of the expected crude product are obtained.

Workup

  1. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated off

Sources & evidence

ORD record
ord-3b93da257f3745efbe86a4dbd806bb1d
Source dataset
uspto-grants-2006_10
Patent number
US07122564B2

Reaction notes

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