Trifluoroacetic acid → HCID 86754339, compound

HRID 583706Notes

Reaction equation

HRID 583706 reaction equation
C([O:5][C:6](=[O:38])[C@@H:7]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH2:8][NH:9][C:10](=[O:27])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]2[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][CH:21]=2)=[CH:13][CH:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:26][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:19][CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([C:10]([NH:9][CH2:8][C@H:7]([NH:28][S:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)(=[O:31])=[O:30])[C:6]([OH:38])=[O:5])=[O:27])=[CH:16][CH:15]=2)[N:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86754340HCID 86754340, compound

Product 1

HCID 86754339HCID 86754339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 30-6 (120 mg, 0.22 mmol) was dissolved in 1 mL CH2Cl2, and 1 mL TFA was added. After 1 h the reaction was concentrated azeotroped with toluene, chromatographed (silica, 18:1:1→9:1:1→CH2Cl2 /MeOH/HOAc) and purified by prep HPLC (C18, 0.1% TFA in H2O/CH3CN) providing 30-7 as a white solid.

Workup

  1. concentrationAfter 1 h the reaction was concentrated
  2. customazeotroped with toluene
  3. customchromatographed (silica, 18:1:1→9:1:1→CH2Cl2 /MeOH/HOAc)
  4. custompurified by prep HPLC (C18, 0.1% TFA in H2O/CH3CN)

Sources & evidence

ORD record
ord-da809920b45b4bc182d1b11456d17e27
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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