Isobutyryl chloride → Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate

HRID 62670

Reaction equation

HRID 62670 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>ClCCl.O>[C:21]([NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])(=[O:25])[CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 62325Isobutyryl chlorideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 71007313Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamateYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (200 mg, 0.689 mmol) in dichloromethane (4 mL) was added isobutyryl chloride (0.08 mL, 0.76 mmol, 1 equiv.) and TEA (0.23 mL, 1.72 mmol, 2.5 equiv.) at 0° C. The reaction was warmed to room temperature and stirred for 16 h. The reaction was then diluted with dichloromethane and water. The organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography (silica gel, EtOAc/hexanes) to afford tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate (0.2 g, 81% yield).

Workup

  1. washThe organic layers were washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography (silica gel, EtOAc/hexanes)

Sources & evidence

ORD record
ord-0b625983cee54cefb2c94de1ba51cf0f
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Linked notes

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