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Dimethyl Sulfoxide → (S)-2-(2-Oxoethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131398
Notes
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Reaction equation

HRID 131398 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C@@H:19]1[CH2:31][CH2:32][OH:33])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C@@H:19]1[CH2:31][CH:32]=[O:33])=[O:17])([CH3:14])([CH3:13])[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69212205(S)-di-tert-Butyl 2-(2-hydroxyethyl)piperazine-1,4-dicarboxylate

Product 1

HCID 86604575(S)-2-(2-Oxoethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-78 °C

Procedure

Combine a solution of oxalyl chloride (0.238 mL, 2.72 mmol) in dichloromethane (25 mL) with dimethyl sulfoxide (0.322 mL, 4.54 mmol) at −78° C. and stir. After 15 minutes, add a solution of (S)-2-(2-hydroxyethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.60 g, 1.82 mmol) in dichloromethane at −78° C. via cannula and stir at −78° C. After one hour, add triethylamine (1.27 mL, 9.08 mmol) and warm to room temperature overnight. Dilute the mixture with saturated aqueous sodium bicarbonate and extract three times with dichloromethane. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure to give the title compound: mass spectrum (APCI): m/z=129.1 (M+1-2BOC).

Workup

  1. waitAfter one hour
  2. temperaturewarm to room temperature overnight
  3. extractionextract three times with dichloromethane
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-88c7d2abe6c143119bc1b1d4c07d0561
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384934B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes