Trifluoroacetic acid → HCID 67346138, compound

HRID 1669484Notes

Reaction equation

HRID 1669484 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13](=[O: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)(C)(C)C>O.C(Cl)Cl>[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][C:13]([OH:45])=[O:12])[CH2:23]3)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67346119HCID 67346119, compound

Product 1

HCID 67346138HCID 67346138, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

TFA (>150 eq) and a few drops of water were added to a stirred solution of methyl 7-(3-tert-butoxy-3-oxopropyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.03 M) in DCM at RT. The reaction was heated at 60° C. (oil bath temp) for 1 h. Further TFA was introduced (circa 60 eq) and heating continued for 2 h. Volatiles were removed in vacuo. The residue was taken up in EtOAc and washed with 1N HCl (aq), brine before being dried (Na2SO4) filtered and concentrated in vacuo. Residual tert-BuOH was removed by sonication in Et2O/PE to afford the product (45%). (ES+) m/z 462 (M+H)+; 484 (M+Na)+.

Workup

  1. temperatureheating
  2. customVolatiles were removed in vacuo
  3. washwashed with 1N HCl (aq), brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customResidual tert-BuOH was removed by sonication in Et2O/PE

Sources & evidence

ORD record
ord-670401266e44424fbfd5299bd307649f
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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