Trifluoroacetic acid → HCID 67346293, compound

HRID 1669444Notes

Reaction equation

HRID 1669444 reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][C:11]([N:13]([CH3:45])[CH2:14][CH2:15][CH:16]1[CH2:23][N:22]2[C:24]3[CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=[CH:28][C:29]=3[C:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:21]2[C:20]2[CH:41]=[CH:42][CH:43]=[CH:44][C:19]=2[O:18][CH2:17]1)=[O:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[CH:31]1([C:30]2[C:29]3[CH:28]=[CH:27][C:26]([C:37]([O:39][CH3:40])=[O:38])=[CH:25][C:24]=3[N:22]3[C:21]=2[C:20]2[CH:41]=[CH:42][CH:43]=[CH:44][C:19]=2[O:18][CH2:17][CH:16]([CH2:15][CH2:14][N:13]([CH3:45])[C:11](=[O:12])[CH2:10][CH2:9][NH:8][CH3:6])[CH2:23]3)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67343754HCID 67343754, compound

Product 1

HCID 67346293HCID 67346293, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 7(R,S)-{2-[[N-(tert-butoxycarbonyl)-N-methyl-β-alanyl](methyl)amino]ethyl}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.09 M) in DCM was treated with TFA (20 eq) and the resulting mixture was stirred overnight at RT. The reaction was diluted with EtOAc and the combined organic layers were washed with sat. aq. NaHCO3 then brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The product was used directly in the next step without further purification. (ES+) m/z 532 (M+H)+.

Workup

  1. washthe combined organic layers were washed with sat. aq. NaHCO3
  2. dry with materialbrine, before being dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was used directly in the next step without further purification

Sources & evidence

ORD record
ord-1672b343226545eeae66e8e6b131b51d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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