Hydrochloric Acid → [[3-(Benzyloxy)-2,2-dimethylpropanoyl](phenyl)amino]acetic acid

HRID 386607Notes

Reaction equation

C([O:3][C:4](=[O:27])[CH2:5][N:6]([C:13](=[O:26])[C:14]([CH3:25])([CH3:24])[CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1>[CH2:17]([O:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]([N:6]([CH2:5][C:4]([OH:27])=[O:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of ethyl[[3-(benzyloxy)-2,2-dimethylpropanoyl](phenyl)amino]acetate from Step C (530. mg, 1.44 mmol) in THF (10 mL), at ambient temperature, was added aqueous 1M NaOH (2.40 mL, 2.40 mmol). The stirred reaction was then heated to 50° C. for 19 hours, before being allowed to cool to ambient temperature. The bulk of the THF was then removed in vacuo, and aqueous 1M HCl (2.4 mL, 2.4 mmol) was then added resulting in an oily biphasic mixture. The mixture was extracted with ethyl acetate (twice) and the combined organics were washed with water and lastly saturated brine. The organics were then dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound which was used without further purification. MS: m/z=342 (M+1).

Workup

customThe stirred reaction
temperatureto cool to ambient temperature
additionwas then added
customresulting in an oily biphasic mixture
extractionThe mixture was extracted with ethyl acetate (twice) and the combined
washorganics were washed with water and lastly saturated brine
dry with materialThe organics were then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5e219a2d98bf4721a15cc6203959a552
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372859B2

Reaction notes

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