Triethylamine → Methyl alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

HRID 1378850Notes

Reaction equation

HRID 1378850 reaction equation
C(C1C=CC(S(N[C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=O)=O)=CC=1)(C)C.C(N(CC)CC)C.[C:45]([Si:49]([CH3:52])([CH3:51])Cl)([CH3:48])([CH3:47])[CH3:46].C[CH2:54][O:55]C(C)=O>ClCCl.CN(C)C1C=CN=CC=1>[Si:49]([O:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[C:14]([O:55][CH3:54])=[O:37])=[C:18]([CH2:25][CH2:26][CH3:27])[CH:19]=1)([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:52])[CH3:51]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 19080378N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamide

Product 1

HCID 22912473Methyl alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetateYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.50 g (6.98 mmol) of the product of Step A dissolved in 20 mL of dichloromethane was added 1.95 mL (14.0 mmol) of triethylamine, 1.26 g (8.38 mmol) of tert-butyldimethylchlorosilane, 85 mg (0.1 eq) of 4-dimethylaminopyridine and the reaction mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. The reaction was then diluted with 100 mL EtOAc, washed with water, 1.0N HCl, saturated aqueous NaHCO3, saturated NaCl, dried (MgSO4), filtered and evaporated in vacuo to afford 3.20 g (97%) of the title compound.

Workup

  1. washwashed with water, 1.0N HCl, saturated aqueous NaHCO3, saturated NaCl
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-aee381b695d74a1eac46e8f3ceb1a07a
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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