Trifluoroacetic acid → HCID 71737231, compound

HRID 1481072Notes

Reaction equation

HRID 1481072 reaction equation
C([O:5][C:6](=[O:34])[C@@H:7]([CH3:33])[C@H:8]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:31]#[N:32])[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[C:18]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:17]=2)=[O:12])[CH3:9])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:31]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[C:18]([O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:17]=2)[C:22]([OH:23])=[C:13]([C:11]([NH:10][C@H:8]([CH3:9])[C@H:7]([CH3:33])[C:6]([OH:34])=[O:5])=[O:12])[N:14]=1)#[N:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89813118HCID 89813118, compound

Product 1

HCID 71737231HCID 71737231, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,3R)-3-[(1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-2-methyl-butyric acid tert-butyl ester (32 mg, 0.069 mmol) in CH2Cl2 (3 mL) was added trifluoroacetic acid (2 mL) at 0° C., and the mixture was stirred at r.t. for 2 h. The mixture was concentrated in vacuo, and the resulting residue was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH ˜2 with 4 M HCl, and the resulting precipitate was isolated by filtration to give 24 mg of the title compound as a pale pink solid. MS: (−) m/z 404.32 (M−1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in saturated NaHCO3
  3. washwashed several times with ether
  4. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-880fbf1df39a436787f950b32b154668
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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