Dimethyl Sulfoxide → HCID 69214655, compound

HRID 131405Notes

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][CH:32]([OH:34])[CH3:33])=[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][C:32](=[O:34])[CH3:33])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

Add oxalyl chloride (2.52 mL, 28.9 mmol) to a solution of dimethyl sulfoxide (3.42 mL, 48.2 mmol) in dichloromethane (130 mL) at −78° C. After 15 minutes at −78° C., add (S)-2-(2-hydroxypropyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester 6.64 g, 19.3 mmol) in dichloromethane (20 mL). Stir the mixture for 1 hour at −78° C., add triethylamine (13.4 mL, 96.4 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. Purify by flash chromatography, eluting with a step gradient (100% dichloromethane to 5% 2N ammonia-methanol in dichloromethane), to obtain (S)-2-(2-oxo-propyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (5.77 g, 87%): mass spectrum (APCI): m/z=143.1 (M+1-2BOC).

Workup

temperaturewarm to room temperature overnight
extractionextract three times with dichloromethane
dry with materialdry over sodium sulfate
concentrationconcentrate under reduced pressure
customPurify by flash chromatography
washeluting with a step gradient (100% dichloromethane to 5% 2N ammonia-methanol in dichloromethane)

Sources & evidence

ORD record: ord-117c924d026a4fc7a0a8526219fc7ce1
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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