Lithium Hydroxide → 2-(4-(TERT-BUTOXYCARBONYL(METHYL)AMINO) PHENYL)ACETIC ACID

HRID 858056Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of [4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-acetic acid methyl ester (prepared according to the procedure of Hay et al. as described in J. Chem. Soc. Perkin Trans I. 1999, 19, 2759) (2.68 mmol) in methanol (10 mL) was added 1.0M aqueous lithium hydroxide solution (13.7 mL) and the mixture heated to 50° C. for 35 mins. The reaction mixture was cooled in an ice bath then washed with ether (25 mL), acidified with 3.0M aqueous hydrochloric acid to pH=4 while stirring and cooling in an ice bath. The precipitate was isolated by filtration, washed with water and dried in vacuo to give [4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-acetic acid as a colorless solid (70%).

Workup

temperatureThe reaction mixture was cooled in an ice bath
washthen washed with ether (25 mL)
temperaturecooling in an ice bath
customThe precipitate was isolated by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-3fa99353c6a047a9af3044ca72328568
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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