Triethylamine → 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

HRID 873309Notes

Reaction equation

[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].[OH:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>CCOCC>[C:18]([O:17][C:16]([NH:15][O:14][S:9]([C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=1[CH3:13])(=[O:11])=[O:10])=[O:22])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Mesitylenesulfonyl chloride (7.75 g, 35.4 mmol) and t-butyl N-hydroxycarbamate (4.72 g, 35.4 mmol) were dissolved in ether (150 mL). Triethylamine (4.88 mL, 35.4 mmol) was added dropwise with stirring at 0° C. The mixture was stirred at 0° C. for 1 h following the addition and the precipitate of triethylamine hydrochloride removed by filtration. The precipitate was washed twice with ether and the washings added to the filtrate. The ether was removed in vacuo and the residue was re-dissolved in the minimum volume of toluene. Petroleum ether 40-60 was added to precipitate N-t-Butoxycarbonyl-β-(mesitylsulfonyl)hydroxylamine as a white solid.

Workup

stirringThe mixture was stirred at 0° C. for 1 h
additionthe addition
customthe precipitate of triethylamine hydrochloride removed by filtration
washThe precipitate was washed twice with ether
additionthe washings added to the filtrate
customThe ether was removed in vacuo
dissolutionthe residue was re-dissolved in the minimum volume of toluene
additionPetroleum ether 40-60 was added
customto precipitate N-t-Butoxycarbonyl-β-(mesitylsulfonyl)hydroxylamine as a white solid

Sources & evidence

ORD record: ord-cb515abd92f54d35afc6cd1e97959308
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975406B2

Reaction notes

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