Trifluoroacetic acid → HCID 18950938, compound

HRID 1492773Notes

Reaction equation

HRID 1492773 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[C:13]2[CH:14]=[C:15]([CH2:18][N:19]3[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:22]([CH3:29])[N:21]=[C:20]3[CH2:30][CH3:31])[CH:16]=[CH:17][C:12]=2[O:11][C:10]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([O:40]C(C)(C)C)=[O:39]>ClCCl>[Br:8][C:9]1[C:13]2[CH:14]=[C:15]([CH2:18][N:19]3[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:22]([CH3:29])[N:21]=[C:20]3[CH2:30][CH3:31])[CH:16]=[CH:17][C:12]=2[O:11][C:10]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131718806HCID 131718806, compound

Product 1

HCID 18950938HCID 18950938, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (7 ml) was added dropwise to a stirred solution of the product of Example 144 (0.892 g) in dichloromethane (30 ml)cooled to 0° C. After 21/2 h the solvent was removed in vacuo to yield an orange oil. The oil was diluted with dichloromethane, washed with hydrochloric acid, dried and the solvent removed in vacuo. The residue was purified by flash column chromatography eluting with dichloromethane/methanol (30:1) to give the title compound as a white solid (200 mg).

Workup

  1. customAfter 21/2 h the solvent was removed in vacuo
  2. customto yield an orange oil
  3. washwashed with hydrochloric acid
  4. customdried
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash column chromatography
  7. washeluting with dichloromethane/methanol (30:1)

Sources & evidence

ORD record
ord-f4c44ef2101649d4a65e320603412e0d
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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