Trifluoroacetic acid → HCID 22823408, compound

HRID 2166800Notes

Reaction equation

HRID 2166800 reaction equation
C([NH:8][C@H:9]([C:14]([NH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23](=[O:27])[O:24]2)=[CH:19][CH:18]=1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])(OC(C)(C)C)=O.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[NH2:8][C@H:9]([C:14]([NH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23](=[O:27])[O:24]2)=[CH:19][CH:18]=1)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22823403HCID 22823403, compound

Product 1

HCID 22823408HCID 22823408, compound

Procedure

The product of Example I, above, (191.5 mg, 0.43 mmol) was dissolved at room temperature in 2 mL of trifluoroacetic acid. After 2 hr, the excess trifluoroacetic acid was removed at 1.6 kPa and room temperature, and the residue was dried at 0.1 Pa overnight. The yield of pale yellow glass was quantitative. It was purified by dissolving in 1 mL of methanol and reprecipitating by adding 30 mL of ether; mp=155.6°; NMR (2/1 CDCl3 /CD3OD) δ(LeuCH3)=1.02 D (6), J=5 Hz, δ(LeuCH2)=1.87 D (2), δ(LeuCH)=4.2 M (1), δ(ArH)=7.6 M (9).

Workup

  1. customthe excess trifluoroacetic acid was removed at 1.6 kPa and room temperature
  2. customthe residue was dried at 0.1 Pa overnight
  3. customIt was purified
  4. dissolutionby dissolving in 1 mL of methanol
  5. customreprecipitating
  6. additionby adding 30 mL of ether

Sources & evidence

ORD record
ord-d67de9922f4048e295dfa9e32a82352e
Source dataset
uspto-grants-1983_06
Patent number
US04388233

Reaction notes

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