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

HRID 1896888Notes

Reaction equation

HRID 1896888 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-51de9674f2404da5b8815d068889f94a
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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