Water → 3-[(Tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid

HRID 901947Notes

Reaction equation

HRID 901947 reaction equation
O.[OH-].[Li+].O.[CH3:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]C)=[O:22])[CH:16]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]>O1CCOCC1>[C:21]([C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:6]([CH3:5])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10])([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59700597Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

Product 1

HCID 224502433-[(Tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (420 mg, 10 mmol) and water (15 ml) were added to a solution of tert-butyl N-methyl-N-(3-(methyloxycarbonyl)benzyl)carbamate (1.6 g, 5.6 mmol) in dioxan (20 ml) and the mixture was stirred for 2 h. The dioxan was removed in vacuo and the residue was taken up in 0.3N potassium hydrogen sulphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water and brine, dried and reduced to afford tert-butyl N-(3-carboxybenzyl)-N-methylcarbamate (1.4 g, 95%).

Workup

  1. customThe dioxan was removed in vacuo
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water and brine
  4. customdried

Sources & evidence

ORD record
ord-bfed7b5070074d4db80fec8494a809e6
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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