Water → HCID 86675028, compound

HRID 472144Notes

Reaction equation

C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH:9]([CH3:11])[CH3:10].[C:14]([O:18][C:19]([NH:21][CH2:22][C@H:23]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:24]([O:26][CH3:27])=[O:25])=[O:20])([CH3:17])([CH3:16])[CH3:15].O>ClCCl>[C:14]([O:18][C:19]([NH:21][CH2:22][C@H:23]([N:28]1[CH2:29][CH2:30][N:31]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[CH2:32][CH2:33]1)[C:24]([O:26][CH3:27])=[O:25])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1.2 ml (8.3 mmol) of triethylamine and then 0.8 ml (7.6 mmol) of isobutyryl chloride are added to a solution of 2.0 g (6.9 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate in 20 ml of dichloromethane, cooled beforehand to 0° C. After stirring at ambient temperature for 1 h 30, water is added. The reaction medium is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude residue obtained is purified by chromatography on silica gel, elution being carried out with a 50/50 heptane/ethyl acetate mixture. 2.0 g (81%) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoate are obtained in the form of a colorless oil.

Workup

additionis added
extractionThe reaction medium is extracted with dichloromethane
washThe organic phase is washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude residue obtained
customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record: ord-45e3a153182b4d0f87babbc0270eb25a
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633196B2

Reaction notes

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