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

HRID 1804553Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:30][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>[O:11]=[C:12]([CH2:30][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]

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 and 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-256f8cb1b192436d987cb21013c8e73b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354418B2

Reaction notes

Loading…