Dimethyl Sulfoxide → HCID 57637086, compound

HRID 2110930Notes

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>[CH2:22]([O:21][C:20](=[O:29])[NH:19][CH2:18][CH2:17][C:15](=[O:16])[NH:14][CH2:13][C:12](=[O:11])[CH:30]([CH3:32])[CH3:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -70 °C

Procedure

10.81 ml (126.08 mmol) oxalyl chloride are placed in 300 ml dichloromethane, 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-4527d8fae3064070b42e4abbfbe36306
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517995B2

Reaction notes

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