Benzyl chloroformate → (1-Cyano-2-methanesulfonyl-1-methyl-ethyl)-carbamic acid benzyl ester

HRID 1480170Notes

Reaction equation

[NH2:1][C:2]([CH3:10])([CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[C:3]#[N:4].CCN(C(C)C)C(C)C.[C:20](Cl)(=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:21][C:20](=[O:29])[NH:1][C:2]([C:3]#[N:4])([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-Amino-3-methanesulfonyl-2-methyl-propionitrile (Example 80a, 5.01 g, 30.9 mmol) in dry THF (119 mL) was added DIEA (12.1 mL, 67.9 mmol) and benzyl carbonochloridate (CAN 501-53-1, 5.57 mL, 37.1 mmol). Reaction was stirred at 45° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and was extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (8.12, 89%) as a yellow oil. MS (ESI, m/z): 297.5 (M+H+).

Workup

customReaction
concentrationThe reaction mixture was concentrated in vacuo
dissolutionThe residue was dissolved in ethylacetate
extractionwas extracted with an 1.0M aqueous solution of sodium bicarbonate
dry with materialThe organic layer was dried over sodium sulfate
customevaporated down to dryness
customThe crude was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record: ord-ac3eb25091604f1da2dc47aee08679fb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

Loading…