Trifluoroacetic acid → HCID 13057012, compound

HRID 1903372Notes

Reaction equation

HRID 1903372 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:30]([NH:32][CH3:33])=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])=[O:16])[C:10](=[O:34])[CH:9]1[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[OH:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][CH:9]2[NH:8][CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:30]([NH:32][CH3:33])=[O:31])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[O:16])[C:10]2=[O:34])=[CH:41][CH:40]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22821055HCID 22821055, compound

Product 1

HCID 13057012HCID 13057012, compound

Procedure

Piperazinone acetyl-gly-phe-NHCH3 11a (0.58 g, 1.0×10-3 mole) and trifluoroacetic acid are stirred at room temperature for 1/2 hour. The solvent is then evaporated and the residue dissolved in CH2Cl2. The CH2Cl2 solution is washed in turn with saturated aqueous NaHCO3 and saturated aqueous NaCl before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate give 12a which is purified by chromatography and the structure corroborated by NMR. NMR (Acetone - d6)δ (d, 3, methyl amide), 3.0-4.3 (m, 14, methylenes and phenolic-OH), 4.53 (m, 1, phenylalanine methine), 6.88 (8, 4, aromatic), 7.25 (s, 5, aromatic), 7.6-8.0 (m, 3, amide NH's).

Workup

  1. customThe solvent is then evaporated
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washThe CH2Cl2 solution is washed in turn with saturated aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationFiltration of the drying agent and evaporation of the filtrate

Sources & evidence

ORD record
ord-bbf28c38d24d44e8a0762a75f68bcc3e
Source dataset
uspto-grants-1984_03
Patent number
US04435571

Reaction notes

Loading…