Propofol → Dodecyl[[2,6-Bis(1-methylethyl)phenoxy]sulfonyl]carbamate

HRID 1769986Notes

Reaction equation

HRID 1769986 reaction equation
[CH2:1]([O:13][C:14](=[O:20])[NH:15][S:16](Cl)(=[O:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[OH:33])([CH3:23])[CH3:22].C(N(CC)CC)C>C1COCC1>[CH2:1]([O:13][C:14](=[O:20])[NH:15][S:16]([O:33][C:25]1[C:26]([CH:30]([CH3:31])[CH3:32])=[CH:27][CH:28]=[CH:29][C:24]=1[CH:21]([CH3:23])[CH3:22])(=[O:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 4943PropofolHCID 8471TriethylamineHCID 10758631Dodecyl(chlorosulfonyl)carbamate

Product 1

HCID 10648021Dodecyl[[2,6-Bis(1-methylethyl)phenoxy]sulfonyl]carbamateYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-dodecyl(chlorosulfonyl)carbamate (5.0 g, 15.2 mmoles) in 80 mL THF was added dropwise to a solution of 2,6-diisopropyl phenol(2.72 g, 15.2 mmoles) and excess triethylamine in 100 mL THF at room temperature under an atmosphere of N2. The mixture was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between 1N HCl and EtOAc. The organic layer was dried with MgSO4, filtered, and evaporated to give a clear oil. Chromatography (SiO2, 5% EtOAc/hexanes) gave 4.26 g of the title compound as a waxy solid, mp 32°-35° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1N HCl and EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a clear oil

Sources & evidence

ORD record
ord-d8213a0a14a74543af1819c1044e671c
Source dataset
uspto-grants-1995_01
Patent number
US05384328

Reaction notes

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