Lithium Hydroxide → 3-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-4-bromo-benzoic acid

HRID 554582Notes

Reaction equation

C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:14][CH3:15])[CH:6]=1)C.[Li+].[OH-]>CO>[CH2:19]([O:18][C:16]([N:13]([CH2:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[Br:11])[C:4]([OH:26])=[O:3])[CH2:14][CH3:15])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-bromo-benzoic acid ethyl ester (3.62 g, 7.2 mmol) was dissolved in MeOH (40 mL) and cooled to 0° C. 1N Aqueous LiOH (22 mL, 22 mmol) was added, and the reaction was stirred at room temperature for 3 hours. The mixture was quenched with 1N aqueous HCl (22 mL) and extracted three times with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to give 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-bromo-benzoic acid, which was combined with the hydrolyzed product isolated in step 5.

Workup

customThe mixture was quenched with 1N aqueous HCl (22 mL)
extractionextracted three times with EtOAc
washThe combined organic layers were washed with brine
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-75915fba56bd4c8baee78b31f44ac1f9
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049015B2

Reaction notes

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