Trifluoroacetic acid → HCID 57741513, compound

HRID 416010Notes

Reaction equation

HRID 416010 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[C:26]([Cl:28])[C:25]([CH2:29][CH:30]4[CH2:34][CH2:33][N:32]([CH:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)[C:31]4=[O:41])=[C:24]([Cl:42])[CH:23]=3)=[CH:18][CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:35]1([N:32]2[CH2:33][CH2:34][CH:30]([CH2:29][C:25]3[C:24]([Cl:42])=[CH:23][C:22]([C:19]4[CH:18]=[CH:17][C:16]([C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[O:15])=[CH:21][CH:20]=4)=[CH:27][C:26]=3[Cl:28])[C:31]2=[O:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57741489HCID 57741489, compound

Product 1

HCID 57741513HCID 57741513, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve racemic 4-[3′,5′-dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.843 g, 1.37 mmol) in dichloromethane (25 mL) and cool in ice bath to 0° C. while stirring under an inert atmosphere. Add triethylsilane (0.5 mL) and trifluoroacetic acid (5.0 mL) to the mixture and allow the temperature to rise to room temperature. Monitor the reaction via TLC. Once starting material is consumed, dilute the reaction with dichloromethane and quench with saturated sodium bicarbonate. Collect the organic phase and the extract aqueous phase with dichloromethane (2×50 mL). Combine organic phases and dry over magnesium sulfate. Extract desired material with resin bound acidic media (SCX) to obtain 0.656 g (93%) of white solid: MS (m/z): 514.0 (M+1).

Workup

  1. customto rise to room temperature
  2. customMonitor the reaction via TLC
  3. customOnce starting material is consumed
  4. additiondilute
  5. customthe reaction with dichloromethane
  6. customquench with saturated sodium bicarbonate
  7. customCollect the organic phase
  8. dry with materialCombine organic phases and dry over magnesium sulfate
  9. extractionExtract desired material with resin

Sources & evidence

ORD record
ord-c6f86788968e4180881ad50ac7149192
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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