Water → [tert-Butoxycarbonyl-(3,4-difluorophenyl)-amino]-acetic acid

HRID 1267909Notes

Reaction equation

HRID 1267909 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][N:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1.O.O.[OH-].[Li+].OS([O-])(=O)=O.[K+]>O1CCCC1>[C:17]([O:16][C:14]([N:5]([CH2:4][C:3]([OH:21])=[O:2])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 54030684[tert-Butoxycarbonyl-(3,4-difluorophenyl)-amino]-acetic acid methyl ester

Product 1

HCID 18542398[tert-Butoxycarbonyl-(3,4-difluorophenyl)-amino]-acetic acidYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [tert-butoxycarbonyl-(3,4-difluorophenyl)-amino]-acetic acid methyl ester (14.7 g) in tetrahydrofuran (100 ml) was added water (100 ml) and lithium hydroxide monohydrate (6.2 g) and reaction mixture stirred at room temperature over-night before removal of tetrahydrofuran at reduced pressure. Residue was acidified to pH 4 by addition of KHSO4 (10% solution in water) and extracted with ethyl acetate. Organic extracts combined, dried (Na2SO4) and concentrated to leave the sub-title compound as a gum (12.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-258ecbd7265e4ca0b11ec325769a57fe
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

Loading…