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

HRID 2272990Notes

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].[C:14]([NH:21][OH:22])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C>C1COCC1>[C:17]([O:16][C:14]([NH:21][O:22][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:15])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-mesitylene sulphonyl chloride (2.0 g, 9.14 mmol) in dry THF (50 mL), is added N-Boc-hydroxylamine (1.21 g, 9.14 mmol) and cooled to 0° C. under N2 atmosphere. The reaction mixture is stirred for 5 minutes. To this mixture triethylamine (1.1 g, 11 mmol) is added slowly over 10 minutes. The reaction mixture is stirred for 1 hour at 0° C. and upon completion, the solvent removed in vacuo. The residue is redissolved in dichloromethane (50 mL) and washed with water (2×50 mL), 10% aqueous NaHCO3 (50 mL) and dried over MgSO4. It is then concentrated under reduced pressure at room temperature to get the product as an off white solid; (2.1 g, 73%). TLC: pet ether/ethyl acetate (8/2) Rf—0.4. 1H NMR (DMSO-d6; 400 MHz): δ 11.16 (s, 1H), 7.12 (s, 2H), 2.49 (s, 6H), 2.28 (s, 3H), 1.23 (s, 9H).

Workup

stirringThe reaction mixture is stirred for 1 hour at 0° C. and upon completion
customthe solvent removed in vacuo
dissolutionThe residue is redissolved in dichloromethane (50 mL)
washwashed with water (2×50 mL), 10% aqueous NaHCO3 (50 mL)
dry with materialdried over MgSO4
concentrationIt is then concentrated under reduced pressure at room temperature
customto get the product as an off white solid

Sources & evidence

ORD record: ord-ac3b2e4202c941aba91bb88b0d2fc48a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120804B2

Reaction notes

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