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

HRID 1771993Notes

Reaction equation

HRID 1771993 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].[OH:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].CCN(CC)CC>CCOCC>[C:2]1([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([O:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamateYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,4,6-trimethylbenzene-1-sulfonyl chloride (30 g, 0.148 mol) and tert-butyl hydroxycarbamate (18 g, 0.148 mol) in Et2O (500 mL) was added Et3N (15 g, 0.148 mol) dropwise over 1 h. The reaction mixture was stirred at room temperature for 4 h, then filtered. The filtrate was concentrated. The product was purified by silica gel column chromatography (5% v/v EtOAc in PE) to give tert-butyl mesitylsulfonyloxycarbamate as a white solid (31 g, yield 72%). ESI MS: m/z 338 [M+Na]+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customThe product was purified by silica gel column chromatography (5% v/v EtOAc in PE)

Sources & evidence

ORD record
ord-0ba9467744e549929db6564fed3632c9
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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