Dimethylformamide → HCID 59351819, compound

HRID 1889300Notes

Reaction equation

HRID 1889300 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:15]=1[NH:21][C:22](=[O:26])OCC)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN(C)C=O>C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:12](=[O:13])[C:14]2[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:15]=2[NH:21][C:22]1=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 59351454HCID 59351454, compound

Product 1

HCID 59351819HCID 59351819, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl (3-{[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]carbonyl}-5-ethyl-2-thienyl)carbamate (0.35 g) and N,N-dimethylformamide (5 mL) was stirred at 150° C. for 1 day. 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 obtained residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.14 g, 45%).

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. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08a5378683a84d21b73406a0b72f2d0d
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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