Sodium Hydroxide → 4-((((Tert-butoxy)carbonyl)amino)methyl)-3-fluorobenzoic acid

HRID 220772Notes

Reaction equation

HRID 220772 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:6]([F:19])[CH:5]=1.[OH-].[Na+]>O1CCOCC1.CCOC(C)=O>[C:15]([O:14][C:12]([NH:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[CH:5][C:6]=1[F:19])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 597677014-(tert-Butoxycarbonylamino-methyl)-3-fluorobenzoic Acid Methyl Ester

Product 1

HCID 230231654-((((Tert-butoxy)carbonyl)amino)methyl)-3-fluorobenzoic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(tert-butoxycarbonylamino-methyl)-3-fluorobenzoic acid methyl ester from Example E3.5 (640 mg, 2.25 mmol) in dioxan (40 ml) was added 1N NaOH (4.5 ml, 4.5 mmol). The mixture was stirred for 18 h, diluted with EtOAc, washed with 1N KHSO4, water and brine and concentrated in vacuo to give a white solid identified as the title compound (608 mg, 100%).

Workup

  1. washwashed with 1N KHSO4, water and brine
  2. concentrationconcentrated in vacuo
  3. customto give a white solid

Sources & evidence

ORD record
ord-55e658be137d45bfb84319c930d0d0ac
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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