Dimethyl Sulfoxide → HCID 57637086, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH:30]([CH3:32])[CH3:31])[CH2:13][NH:14][C:15]([CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:16].C(N(CC)CC)C>ClCCl>[CH3:31][CH:30]([CH3:32])[C:12](=[O:11])[CH2:13][NH:14][C:15]([CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
10.81 ml (126.08 mmol) oxalyl chloride are placed in 300 ml dichloromethane and cooled to −70° C. 11.94 ml (168.11 mmol) dimethylsulphoxide are slowly added dropwise. The mixture is stirred for 0.1 hours, then 32.40 g (105.07 mmol) benzyl [2-(2-hydroxy-3-methyl-butylcarbamoyl)-ethyl]-carbamate in 70 ml dichloromethane are added. The mixture is stirred for 1 hour, then 62.48 ml (450.72 mmol) triethylamine are added dropwise. The reaction mixture is stirred for 1.5 hours at −70° C., then slowly allowed to come up to ambient temperature. It is diluted with dichloromethane and washed with 1 molar hydrochloric acid, saturated sodium carbonate solution, water and saturated sodium chloride solution. The organic phase is dried and evaporated to dryness.
Workup
- stirringThe mixture is stirred for 1 hour
- stirringThe reaction mixture is stirred for 1.5 hours at −70° C.
- customto come up to ambient temperature
- washwashed with 1 molar hydrochloric acid, saturated sodium carbonate solution, water and saturated sodium chloride solution
- customThe organic phase is dried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-f7189c1099284edcaa2d54c7b977bf68
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354418B2
Reaction notes
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