Trifluoroacetic acid → HCID 67344803, compound

HRID 1669486Notes

Reaction equation

HRID 1669486 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:46])[CH2:15][CH2:16][CH:17]2[CH2:24][N:23]3[C:25]4[CH:26]=[C:27]([C:38]([O:40][CH3:41])=[O:39])[CH:28]=[CH:29][C:30]=4[C:31]([CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[C:22]3[C:21]3[CH:42]=[CH:43][CH:44]=[CH:45][C:20]=3[O:19][CH2:18]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:32]1([C:31]2[C:30]3[CH:29]=[CH:28][C:27]([C:38]([O:40][CH3:41])=[O:39])=[CH:26][C:25]=3[N:23]3[C:22]=2[C:21]2[CH:42]=[CH:43][CH:44]=[CH:45][C:20]=2[O:19][CH2:18][CH:17]([CH2:16][CH2:15][C:14](=[O:46])[N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:24]3)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67345211HCID 67345211, compound

Product 1

HCID 67344803HCID 67344803, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 7-{3-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-oxopropyl}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.04 M) in DCM was treated with TFA (170 eq) and stirred at RT overnight. The volatiles were then removed in vacuo and the residue partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the product as an off-white foam (100%) that was used without further purification. (ES+) m/z 530 (M+H)+.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customthe residue partitioned between sat. aq. NaHCO3 and EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b5e2bb67cc24d928561f6b6b0180b87
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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