Dimethyl Sulfoxide → HCID 58200258, compound
Reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19](=[O:31])[NH:20][CH:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22]CO)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH2:11]([O:18][C:19](=[O:31])[NH:20][CH:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][CH2:2][CH:1]=[O:5])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
To a stirred solution of oxalyl chloride (1.6 mL, 18.2 mmol) in methylene chloride (20 mL) at −50° C. was added drop-wise a solution of DMSO (2.84 g, 36.4 mmol). The resulting mixture was stirred at −50° C. for 15 minutes, and a solution of (3-hydroxy-1-phenyl-propyl)-carbamic acid benzyl ester (4.7 g, 16.53 mmol) in methylene chloride 35 mL). The mixture was stirred at −50° C. for 15 minutes, then TEA (11.5 mL, 82.7 mmol) was added. The mixture was stirred for five minutes at −50° C., then allowed to stir at room temperature for 30 minutes. The reaction mixture was washed with 5% aqueous HCl, dried over MgSO4, filtered and concentrated under reduced pressure to give 4.7 g (100%) of (4-oxo-1-phenyl-butyl)-carbamic acid benzyl ester as a pale yellow oil.
Workup
- stirringThe mixture was stirred at −50° C. for 15 minutes
- stirringThe mixture was stirred for five minutes at −50° C.
- stirringto stir at room temperature for 30 minutes
- washThe reaction mixture was washed with 5% aqueous HCl
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ae4dfa762cd14fdf89c421a09e268bf3
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871760B2
Reaction notes
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