Dimethyl Sulfoxide → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

HRID 2066906Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[O:11]=[CH:12][C@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of oxalyl chloride (90 mL, 1.03 mol) in CH2Cl2 was added dropwise a solution of DMSO (100 mL, 1.41 mol) in CH2Cl2. The mixture was stirred at −78° C. for 1 hr, and a solution of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate (90 g, 0.51 mol) in CH2Cl2 was added. After stirring for 3 hr, 500 mL of triethylamine was added and the reaction mixture was stirred for another 3 h at −78° C. The reaction was quenched with 1% HCl and the reaction mixture was warmed to RT. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The organic layer was washed with water, dried over MgSO4, and evaporated to provide crude N.1, (R)-tert-butyl 1-oxopropan-2-ylcarbamate (76.0 g, 85.4%). 1H NMR (CDCl3) δ 9.56 (s, 1H), 4.23 (br s, 1H), 1.45 (s, 9H), 1.32 (s, 3H).

Workup

stirringAfter stirring for 3 hr
stirringthe reaction mixture was stirred for another 3 h at −78° C
customThe reaction was quenched with 1% HCl
temperaturethe reaction mixture was warmed to RT
customThe organic layer was separated
extractionthe aqueous layer was extracted with CH2Cl2
washThe organic layer was washed with water
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-939843881b6347eda17a24d99fac6e5c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293752B2

Reaction notes

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