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Water → HCID 86675028, compound

HRID 2202198
Notes
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Reaction equation

HRID 2202198 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 86675027Methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate

Product 1

HCID 86675028HCID 86675028, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

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

Sources & evidence

ORD record
ord-b3a5206ed4bc4a64b106d73ca0504eee
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365529B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes