Trifluoroacetic acid → HCID 11649435, compound

HRID 732806Notes

Reaction equation

HRID 732806 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-c0416f7e4b4344448d44bf76d35a6fad
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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