Sodium Hydroxide → 4-((Tert-butoxycarbonylamino)methyl)-3-methylbenzoic acid

HRID 220767Notes

Reaction equation

HRID 220767 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]([CH3:19])[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[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[CH3:19])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 575552214-(tert-Butoxycarbonylamino-methyl)-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575554314-((Tert-butoxycarbonylamino)methyl)-3-methylbenzoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(tert-Butoxycarbonylamino-methyl)-3-methyl-benzoic acid methyl ester from Example E2h.3 (1.04 g, 3.7 mmol) was dissolved in dioxan (20 ml). 1N NaOH solution (5.6 ml, 5.6 mmol) was added and the mixture was stirred for 18 h at room temperature then concentrated in vacuo. The residue was redissolved in EtOAc, washed with 1N KHSO4 then brine, dried and concentrated in vacuo to yield the title compound (800 mg, 81%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was redissolved in EtOAc
  3. washwashed with 1N KHSO4
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ba7a635ec8a40ee86adf0535820d791
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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