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

HRID 2110923Notes

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>ClCCl>[O:29]=[C:26]([CH2:27][CH3:28])[CH2:25][NH:24][C:23]([CH2:22][CH2:21][NH:20][C:19](=[O:31])[O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:30]

Participants

Conditions

Temperature: -53 °C

Procedure

2.20 ml (26.05 mmol) oxalyl chloride are placed in 10 ml dichloromethane, the solution is cooled to −53° C. 2.45 ml (34.49 mmol) dimethylsulphoxide in 5 ml dichloromethane are slowly added dropwise, the mixture is stirred for 0.25 hours, then a solution of 6.30 g (21.40 mmol) benzyl[2-(2-hydroxy-butylcarbamoyl)-ethyl]-carbamate in 30 ml dichloromethane is added. The mixture is stirred for 1.5 hours at −60° C., then 12.60 ml triethylamine are added dropwise. The suspension is stirred for 1 hour at −50° C., then within 16 hours allowed to come up to ambient temperature. The reaction mixture is diluted with dichloromethane, extracted with 1 molar hydrochloric acid, 1 molar sodium carbonate solution and water. The organic phase is dried and evaporated to dryness.

Workup

stirringThe mixture is stirred for 1.5 hours at −60° C.
stirringThe suspension is stirred for 1 hour at −50° C.
waitwithin 16 hours allowed
customto come up to ambient temperature
extractionextracted with 1 molar hydrochloric acid, 1 molar sodium carbonate solution and water
customThe organic phase is dried
customevaporated to dryness

Sources & evidence

ORD record: ord-cbe59506c9bd4f0ea96a08a81a20de08
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517995B2

Reaction notes

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