Water → HCID 86675029, compound

HRID 1966128Notes

Reaction equation

[CH3:1][CH:2]([CH3:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].[C:9]([O:13][C:14]([NH:16][CH2:17][C@H:18]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:19]([O:21][CH3:22])=[O:20])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.O>ClCCl>[C:9]([O:13][C:14]([NH:16][CH2:17][C@H:18]([N:23]1[CH2:24][CH2:25][N:26]([S:4]([CH2:3][CH:2]([CH3:8])[CH3:1])(=[O:6])=[O:5])[CH2:27][CH2:28]1)[C:19]([O:21][CH3:22])=[O:20])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

479 mg (3.0 mmol) of 2-methylpropane-1-sulfonyl chloride are added to a solution of 800 mg (2.8 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate (prepared as described in example 23.1) and 775 μl (5.5 mmol) of triethylamine in 8 ml of dichloromethane, cooled beforehand to 0° C. The reaction medium is stirred at ambient temperature for 18 h and then water is added and the medium is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 5/5 heptane/ethyl acetate mixture. 785 mg (71%) of methyl (S)-3-tert-butoxycarbonylamino-2-[4-(2-methylpropane-1-sulfonyl)piperazin-1-yl]propanoate are obtained in the form of a colorless oil.

Workup

extractionthe medium is extracted with dichloromethane
washThe organic phase is washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue obtained
customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record: ord-548e0a813b024c2ea0281c44b10e5af3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420632B2

Reaction notes

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