Lithium hydroxide, monohydrate → (2-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)acetic acid

HRID 1612400Notes

Reaction equation

HRID 1612400 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O.[OH-].[Li+]>O1CCCC1.O>[C:16]([O:15][C:13]([NH:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][C:3]([OH:20])=[O:2])=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53438887Methyl (2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acetate

Product 1

HCID 2755928(2-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5a in tetrahydrofuran (0.3 M) at room temperature was added a solution of lithium hydroxide monohydrate (1.2 M) in H2O (0.4 M). The reaction was stirred at room temperature overnight. The tetrahydrofuran was removed under reduced pressure. The remaining aqueous phase was acidified with concentrated hydrochloric acid. The precipitated product was filtered off and dried to afford a white solid. (98%) 1H NMR (400 MHz, DMSO-d6) δ 12.34 (br s, 1H), 7.29 (m, 1H), 7.19 (m, 4H), 4.12 (m, 2H), 3.65 (s, 2H), 1.38 (s, 9H).

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. filtrationThe precipitated product was filtered off
  3. customdried
  4. customto afford a white solid

Sources & evidence

ORD record
ord-3820282c779b485a9fde795223f56f50
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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