Triethylamine → HCID 53968692, compound

HRID 2289684Notes

Reaction equation

HRID 2289684 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=1[CH2:22][C:23](O)=[O:24])([CH3:9])[CH3:8].[S:26](=[O:50])(=[O:49])([O:28][C:29]1[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][C:32]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])=[CH:31][C:30]=1[CH:46]([CH3:48])[CH3:47])[NH2:27].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O>[C:42]([Si:39]([CH3:41])([CH3:40])[O:38][C:32]1[CH:31]=[C:30]([CH:46]([CH3:48])[CH3:47])[C:29]([O:28][S:26](=[O:50])(=[O:49])[NH:27][C:23](=[O:24])[CH2:22][C:11]2[C:10]([CH:7]([CH3:8])[CH3:9])=[CH:15][C:14]([CH:16]([CH3:18])[CH3:17])=[CH:13][C:12]=2[CH:19]([CH3:21])[CH3:20])=[C:34]([CH:35]([CH3:37])[CH3:36])[CH:33]=1)([CH3:43])([CH3:45])[CH3:44]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 105156412,4,6-Triisopropylphenylacetic acidHCID 18698847HCID 18698847, compound

Product 1

HCID 53968692HCID 53968692, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Oxalyl chloride (2.45 mL, 28 mmol) was added dropwise to a solution of 2,4,6-triisopropylphenyl acetic acid (5.66 g, 21.6 mmol) in 150 mL toluene with 4 drops of N,N-dimethylformamide as a catalyst. The resulting solution was stirred for 6 hours and then concentrated in vacuo. The residue was redissolved in 150 mL dichloromethane. 4-(Tert-butyl-dimethyl-silanyloxy)-2,6-diisopropylphenyl sulfamate (8.36 g, 21.6 mmol) and triethylamine (7.5 mL, 54 mmol) were added, and the resulting mixture was stirred overnight. Washed with 1M HCl, dried the organic layer over magnesium sulfate, filtered, and concentrated to give 9.86 g of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(tert-butyl-dimethyl-silanyloxy)-2,6-diisopropyl-phenyl ester.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in 150 mL dichloromethane
  3. stirringthe resulting mixture was stirred overnight
  4. washWashed with 1M HCl
  5. dry with materialdried the organic layer over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-042aa90709b84092be96fe4fe76451ba
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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