Trifluoroacetic acid → HCID 54159988, compound

HRID 1279128Notes

Reaction equation

HRID 1279128 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23](=[O:37])[NH:24][CH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([NH2:36])=[N:31][CH:30]=[CH:29]2)=[O:17])(C)(C)C>ClCCl>[NH2:36][C:32]1[C:33]2[C:28](=[CH:27][C:26]([CH2:25][NH:24][C:23]([C@@H:19]3[CH2:20][CH2:21][CH2:22][N:18]3[C:16](=[O:17])[C@H:15]([NH2:14])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:37])=[CH:35][CH:34]=2)[CH:29]=[CH:30][N:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54572064HCID 54572064, compound

Product 1

HCID 54159988HCID 54159988, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.0 mL) was added to 150 mg of (2-{2(S)-[(1-amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-1(R)-phenyl-ethyl)-carbamic acid tert-butyl ester (prepared according to the procedures described in example 110) in 3.0 mL dichloromethane. Stirring was continued for 2h at ambient temperature. The solvent was removed i.vac, the residue was dissolved in methanol and applied to a reversed-phase chromatography column (lenght 100 mm, diameter 14 mm; Merck Lichroprep RP-18, 15-25μ). Elution was started with 25 mL of methanol/water containing 0.3% acetic acid (10:90), then a linear gradient to pure methanol over a period of 75 mL was applied followed by 50 mL of pure methanol. Fractions of 5 mL each were sampled. The solvent was removed to give 75 mg (62%) of the title compound. MS: 404.

Workup

  1. customprepared
  2. customThe solvent was removed i.vac
  3. dissolutionthe residue was dissolved in methanol
  4. washElution
  5. waita linear gradient to pure methanol over a period of 75 mL was applied followed by 50 mL of pure methanol
  6. aliquotFractions of 5 mL each were sampled
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-42470a72382b46c988f33e94cf4e7466
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

Loading…