Trifluoroacetic acid → 2-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-2-propyl-pentanoic acid

HRID 1480955Notes

Reaction equation

HRID 1480955 reaction equation
C([O:5][C:6](=[O:38])[C:7]([CH2:14][NH:15][C:16]([C:18]1[N:19]=[C:20]([C:36]#[N:37])[C:21]2[C:26]([C:27]=1[OH:28])=[CH:25][CH:24]=[C:23]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:22]=2)=[O:17])([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:36]([C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]([O:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:22]=2)[C:27]([OH:28])=[C:18]([C:16]([NH:15][CH2:14][C:7]([CH2:11][CH2:12][CH3:13])([CH2:8][CH2:9][CH3:10])[C:6]([OH:38])=[O:5])=[O:17])[N:19]=1)#[N:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 898129762-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-2-propyl-pentanoic acid tert-butyl ester

Product 1

HCID 898129282-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-2-propyl-pentanoic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-{[(1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-2-propyl-pentanoic acid tert-butyl ester (180 mg), TFA (5 mL) and DCM (5 mL) was stirred at rt overnight; then concentrated, the residue was dissolved in water and added 2 M HCl solution, solids were collected via filtration, washed with water and air dried to give the desired product (150 mg). LC MS ESI+: 462 (M+1)+.

Workup

  1. concentrationthen concentrated
  2. dissolutionthe residue was dissolved in water
  3. additionadded 2 M HCl solution, solids
  4. filtrationwere collected via filtration
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-3293601019d84da3b9ee48bd9e7d8e07
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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