Water → Tert.-butyl 2-[(5-bromo-thiophen-2-yl)-carbonylamino]-isobutyrate

HRID 15101Notes

Reaction equation

HRID 15101 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.Cl.[NH2:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].O>ClCCl>[Br:1][C:2]1[S:6][C:5]([C:7]([NH:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 3491155-Bromothiophene-2-carboxylic acidHCID 12186776Tert-butyl 2-amino-2-methylpropanoate hydrochloride

Product 1

HCID 68638345Tert.-butyl 2-[(5-bromo-thiophen-2-yl)-carbonylamino]-isobutyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.63 g (12.3 mmol) 5-bromo-thiophene-2-carboxylic acid are refluxed in 15 ml dichloromethane together with 7.0 ml of thionyl chloride for 2 h with stirring. The mixture is then evaporated down i. vac. and the residue is twice taken up in toluene and evaporated down completely i. vac. The residue is added dropwise to 10 ml dichloromethane with stirring at ambient temperature in a mixture of 2.41 g (12.3 mmol) tert.-butyl 2-amino-isobutyrate hydrochloride in 20 ml dichloromethane with 5.14 ml (36.9 mmol) TEA and stirred for 16 h. The mixture is poured into water and extracted with dichloromethane, the combined organic phases are dried over magnesium sulphate and evaporated down i. vac.

Workup

  1. customThe mixture is then evaporated down i
  2. customevaporated down completely
  3. additionThe residue is added dropwise to 10 ml dichloromethane
  4. stirringstirred for 16 h
  5. extractionextracted with dichloromethane
  6. dry with materialthe combined organic phases are dried over magnesium sulphate
  7. customevaporated down i

Sources & evidence

ORD record
ord-85ce16b4205a42c8bd3450e8ff110de5
Source dataset
uspto-grants-2010_06
Patent number
US07732466B2

Reaction notes

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