Trifluoroacetic acid → HCID 86610938, compound

HRID 1592979Notes

Reaction equation

HRID 1592979 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](O)[C@H](OCC)C(OC)=O)=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.C([SiH]([CH2:38][CH3:39])CC)C.[C:40]([O:43][CH2:44]C)(=[O:42])[CH3:41].[OH-:46].[Na+].FC(F)(F)[C:50](O)=[O:51]>>[CH2:38]([O:46][C@@H:41]([C@H:50]([OH:51])[C:16]1[CH:15]=[CH:14][C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:11]=1[CH2:10][NH:9][CH3:8])[C:40]([O:43][CH3:44])=[O:42])[CH3:39]

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 86598940HCID 86598940, compound

Product 1

HCID 86610938HCID 86610938, compoundYield 100%

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-6e5dd99a3f8f45f085e53a7275b4e4de
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

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