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Dimethyl Sulfoxide → Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

HRID 601619
Notes
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Reaction equation

HRID 601619 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19](=[O:31])[NH:20][CH2:21][CH2:22][C:23](=[O:30])[NH:24][CH2:25][CH:26]([OH:29])[CH2:27][CH3:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([O:18][C:19](=[O:31])[NH:20][CH2:21][CH2:22][C:23](=[O:30])[NH:24][CH2:25][C:26](=[O:29])[CH2:27][CH3:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57637120Benzyl [2-(2-hydroxybutylcarbamoyl)ethyl]carbamate

Product 1

HCID 57637089Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

To a stirred solution of oxalyl chloride (2 M in DCM) (13.35 ml, 26.5 mmol) in dry DCM at −78° C. is added dropwise DMSO (2.5 ml, 35.4 mmol). After stirring for 15 minutes, the reaction mixture is treated with a solution of [2-(2-hydroxy-butylcarbamoyl)-ethyl]-carbamic acid benzyl ester (step 1) (6.5 g, 22.1 mol) in dry DCM (40 ml). Triethylamine (13 ml) is added after 1 hour and after stirring at −78° C. for 90 minutes, the reaction mixture is allowed to warm to room temperature. The reaction is diluted with DCM (100 ml) and washed with HCl (1M, 200 ml), saturated sodium bicarbonate solution (200 ml), water (200 ml) and brine (200 ml). The organic portion is dried over MgSO4, filtered and concentrated in vacuo to yield the titled compound as a white solid.

Workup

  1. stirringafter stirring at −78° C. for 90 minutes
  2. washwashed with HCl (1M, 200 ml), saturated sodium bicarbonate solution (200 ml), water (200 ml) and brine (200 ml)
  3. dry with materialThe organic portion is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13da29cbac134efe96832c23a46907f0
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902375B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes