Water → 3-(2-{[(Tert-butoxy)carbonyl]amino}-4-chlorophenyl)prop-2-enoic acid

HRID 1991048Notes

Reaction equation

C[O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[OH-].[Na+].O>CO>[C:17]([O:16][C:14]([NH:13][C:7]1[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=1/[CH:5]=[CH:4]/[C:3]([OH:21])=[O:2])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

(E)-3-(2-tert-Butoxycarbonylamino-4chlorophenyl)-acrylic acid methyl ester (4.6 g, 14.7 mmol) was dissolved in MeOH (300 ml), 2N NaOH (11 ml, 22 mmol) and water (147 ml) added and stirred at 50° C. for 1 hour. The clear reaction mixture was concentrated to ˜150 ml, acidified to pH 3 and extracted twice with TBME. The combined organic phases were dried over Na2SO4 and evaporated to dryness to yield the title acid as colorless crystals (3.8 g, 87%).

Workup

concentrationThe clear reaction mixture was concentrated to ˜150 ml
extractionextracted twice with TBME
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-fc9275ce7c314ae89d6d985633c2b88c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645760B2

Reaction notes

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