Trifluoroacetic acid → HCID 66874754, compound

HRID 1799639Notes

Reaction equation

HRID 1799639 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH2:15]([O:22][C:23](=[O:47])[CH2:24][CH:25]([NH:30][C:31](=[O:46])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH:40][C:41]1[CH:45]=[CH:44][S:43][CH:42]=1)[CH2:26][N:27]([CH3:29])[CH3:28])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23](=[O:47])[CH2:24][CH:25]([NH:30][C:31](=[O:46])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]1[CH:45]=[CH:44][S:43][CH:42]=1)[CH2:26][N:27]([CH3:28])[CH3:29])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 66874546HCID 66874546, compound

Product 1

HCID 66874754HCID 66874754, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylsilane (0.23 mL, 1.43 mmol) and trifluoroacetic acid (0.21 mL, 2.9 mmol) were added to a solution of 4-dimethylamino-3-(10-thiophen-3-yl-dec-9-enoylamino)-butyric acid benzyl ester (67 mg, 0.14 mmol) in toluene (8 mL). The reaction mixture was stirred at room temperature for 12 hours after which time the solution was added to cold saturated aq. sodium bicarbonate solution. The aqueous phase was separated and extracted twice with dichloromethane. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 4-dimethylamino-3-(10-thiophen-3-yl-decanoylamino)-butyric acid benzyl ester (74 mg), m/e=473.3 ([M+H]+).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d277c06f7bf46acbf85ad873b0e1804
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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