Sodium Hydroxide → HCID 67411497, compound

HRID 1403674Notes

Reaction equation

HRID 1403674 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:8]([Br:21])[CH:7]=1>O.CO>[Br:21][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:5]([OH:22])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67409341HCID 67409341, compound

Product 1

HCID 67411497HCID 67411497, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

NaOH (48.8 g, 1.22 mol, 2.0 eq) in H2O (1.26 L) was added to a solution of 3-bromo-4-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (210 g, 0.61 mol, 1.0 eq) in MeOH (1.26 L). The reaction mixture was stirred at 50° C. for 2 hrs. The reaction was cooled to room temperature and concentrated to half volume. The residue was acidified to pH 5 by adding 1M HCl solution. The resulting solid was collected and dried to give the title intermediate (200 g, 99.4% yield) as white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated to half volume
  3. additionby adding 1M HCl solution
  4. customThe resulting solid was collected
  5. customdried

Sources & evidence

ORD record
ord-50475b8964fa4a03ad3bae010ef454da
Source dataset
uspto-grants-2014_12
Patent number
US08912209B2

Reaction notes

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