Sodium Hydroxide → 2-(((Benzyloxy)carbonyl)(7-(trifluoromethyl)isoquinolin-1-yl)amino)acetic acid

HRID 2175570Notes

Reaction equation

HRID 2175570 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=2)[CH:20]=[CH:19][N:18]=1)[CH2:12][C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:29])([F:30])[F:28])[CH:25]=2)[CH:20]=[CH:19][N:18]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58562656Methyl 2-(((benzyloxy)carbonyl)(7-(trifluoromethyl)isoquinolin-1-yl)amino)acetate

Product 1

HCID 585626512-(((Benzyloxy)carbonyl)(7-(trifluoromethyl)isoquinolin-1-yl)amino)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanolic solution of methyl 2-(((benzyloxy)carbonyl)(7-(trifluoromethyl)isoquinolin-1-yl)amino)acetate (241 mg, 0.58 mmol) from above step G was cooled in an ice bath and treated with a solution of 1N NaOH (2.88 ml, 2.88 mmol). The solution was stirred for 4 h (monitored with TLC for completion), MeOH evaporated under vacuum (no heat), and the residue treated with 1N HCl and extracted with EtOAc. The EtOAc layer was washed with saturated NaCl, dry over Na2SO4 and evaporated to give the title compound.

Workup

  1. customevaporated under vacuum (
  2. temperatureno heat), and the residue
  3. additiontreated with 1N HCl
  4. extractionextracted with EtOAc
  5. washThe EtOAc layer was washed with saturated NaCl
  6. dry with materialdry over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-afb28ff68fed434eb3d997532371406a
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

Loading…