Trifluoroacetic acid → HCID 11649435, compound

HRID 748940Notes

Reaction equation

HRID 748940 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[CH:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=2)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[CH2:23][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)=[CH:27][CH:26]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68514413HCID 68514413, compound

Product 1

HCID 11649435HCID 11649435, compoundYield 675.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the compound of Example 76 (185.2 mg, 0.33 mmol), Et3SiH (0.3 mL, 1.88 mmol) and TFA (0.3 mL, 3.8 mmol) in CH2Cl2 (30 mL). Stir at room temperature for 1 hour. Quench with saturated aqueous NaHCO3 and extract with 25% i-PrOH in CH2Cl2. Dry over Na2SO4, filter and concentrate. Purify the crude material by flash chromatography (0-5% MeOH/CH2Cl2 to afford 1.18 g of the title compound (63%). LCMS: m/z=530 (M+H)+

Workup

  1. customQuench with saturated aqueous NaHCO3
  2. extractionextract with 25% i-PrOH in CH2Cl2
  3. dry with materialDry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude material by flash chromatography (0-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-efed435d55b54a468913f7530cc1b3bf
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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