Dichloromethane → HCID 59351454, compound

HRID 1889299Notes

Reaction equation

HRID 1889299 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[C:5]([C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15])[CH:4]=1)[CH3:2].[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C.C(Cl)Cl>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Si:24]([O:19][CH2:18][CH2:17][NH:16][C:14]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[S:7][C:6]=1[NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[O:15])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 59351818HCID 59351818, compound

Product 1

HCID 59351454HCID 59351454, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl (5-ethyl-3-{[(2-hydroxyethyl)amino]carbonyl}-2-thienyl)carbamate (0.22 g), tert-butyl(chloro)dimethylsilane (0.15 mL), triethylamine (0.1 g), N,N-dimethylpyridin-4-amine (0.012 g) and methylene chloride (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.35 g, 95%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-93061f10ff26402585d059ac6af3f0a8
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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