Hydrochloric Acid → 2-Benzyl-3-[(tert-butoxycarbonyl)amino]propanoic acid

HRID 1510231Notes

Reaction equation

[CH2:1]([CH:8]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([CH:8]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 2-benzyl-3-[(tert-butoxycarbonyl)amino]propanoate (310 mg) in tetrahydrofuran (15 mL) were added 1N sodium hydroxide aqueous solution (6.0 mL) and the mixture was stirred at 60° C. for 5 hours. The mixture was cooled and adjusted to pH=2 by addition of 1N HCl. The mixture was extracted with ethyl acetate and the separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford 2-benzyl-3-[(tert-butoxycarbonyl)amino]propanoic acid (228 mg) as an crude oil.

Workup

temperatureThe mixture was cooled
extractionThe mixture was extracted with ethyl acetate
washthe separated organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-023bf57f92ae465baa06ffdac4709b11
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211919B2

Reaction notes

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