Trifluoroacetic acid → HCID 54159988, compound

HRID 1008600Notes

Reaction equation

HRID 1008600 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 2 h at ambient temperature. The solvent was removed i.vac, the residue was dissolved in methanol and applied to a reversed-phase chromatography column (length 100 mm, diameter 14 mm; Merck Lichroprep RP-18, 15-25 μ). 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-9169dc70328c4b79bad36922a90b0880
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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