Sodium hydride → Ethyl 2-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxybenzyl)-1,3-dithian-2-carboxylate

HRID 2222448Notes

Reaction equation

HRID 2222448 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[S:20]1[CH2:25][CH2:24][CH2:23][S:22][CH:21]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].[H-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:12]([O:11][C:10]([NH:9][CH2:8][C:7]1[CH:17]=[C:3]([CH:4]=[CH:5][C:6]=1[O:18][CH3:19])[CH2:2][C:21]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:20][CH2:25][CH2:24][CH2:23][S:22]1)=[O:16])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 88552Ethyl 1,3-dithiane-2-carboxylateHCID 59712454HCID 59712454, compound

Product 1

HCID 59712358Ethyl 2-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxybenzyl)-1,3-dithian-2-carboxylate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.76 g of t-butyl N-[5-(bromomethyl)-2-methoxybenzyl]carbamate and 0.76 ml of ethyl 1,3-dithian-2-carboxylate were dissolved in anhydrous N,N-dimethylformamide. A solution of 220 mg of 60% sodium hydride in 18 ml of toluene was added under ice-cooling, and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 1.70 g of the title compound from the 3:1 hexane-ethyl acetate fraction.

Workup

  1. temperaturecooling
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22138a5ef286410ba207ecc02e19e775
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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