Water → HCID 58009627, compound

HRID 450758Notes

Reaction equation

HRID 450758 reaction equation
[C:1]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[K+].Cl[CH2:23][C:24]1[S:28][CH:27]=[C:26]([C:29]([O:31][CH3:32])=[O:30])[CH:25]=1.O>CN(C=O)C.C(OCC)(=O)C>[C:12]([O:11][C:9]([N:8]([CH2:23][C:24]1[S:28][CH:27]=[C:26]([C:29]([O:31][CH3:32])=[O:30])[CH:25]=1)[C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 279800Di-tert-butyl IminodicarboxylateHCID 12926494Methyl 5-(chloromethyl)thiophene-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 58009627HCID 58009627, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.69 g of di-tert-butyl imidodicarbonate in 54 ml of DMF was added 1.91 g of potassium tert-butoxide at 0° C. under argon, followed by stirring at room temperature for 1 hour. A solution of 2.7 g of methyl 5-(chloromethyl)thiophene-3-carboxylate in 8.1 ml of DMF was slowly added thereto, followed by stirring at room temperature overnight. Water and ethyl acetate were added to the reaction solution, followed by carrying out an extraction operation, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 4.394 g of methyl 5-{[bis(tert-butoxycarbonyl)amino]methyl}thiophene-3-carboxylate.

Workup

  1. stirringby stirring at room temperature overnight
  2. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7e3c99b2368442f0a242285c6a6f8a09
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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