Triethylsilane → HCID 69429205, compound

HRID 1375920Notes

Reaction equation

HRID 1375920 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:33][C:34](=[O:36])[CH3:35])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=O)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[C:9]([O:8][CH2:7][C:6]([NH:33][C:34](=[O:36])[CH3:35])([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69429001Acetic acid 2-acetoxymethyl-2-acetylamino-4-(4'-hexanoyl-biphenyl-4-yl)-butyl ester

Product 1

HCID 69429205HCID 69429205, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of acetic acid 2-acetoxymethyl-2-acetylamino-4-(4′-hexanoyl-biphenyl-4-yl)-butyl ester (prepared according to Scheme 1) (1 mmol) in trifluoroacetic acid (10 mL) is added triethylsilane (2.5 mmol). The resulting mixture is stirred at room temperature for 12 h. After concentrating under reduced pressure, the residue is dissolved in DCM and the organic solution is washed with saturated NaHCO3 and brine and dried over Na2SO4. After concentration, the crude product is purified by column chromatography using EtOAc/hexane (1/1) to give the desired compound as a white solid. MS: (ES+): 482.3 (M+1)+.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. dissolutionthe residue is dissolved in DCM
  3. washthe organic solution is washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-f0a7b10285314c0b9772b3fce7a2d8ec
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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