Water → HCID 18322390, compound

HRID 1698893Notes

Reaction equation

HRID 1698893 reaction equation
[CH3:1][NH2:2].[C:3]([NH:13][C:14]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[S:16][C:15]=1[C:23]([O:25]C)=O)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[C-]#N.[Na+].O>CO>[CH3:1][NH:2][C:23]([C:15]1[S:16][C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:18][C:14]=1[NH:13][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8929Sodium CyanideHCID 18322361HCID 18322361, compound

Product 1

HCID 18322390HCID 18322390, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a saturated solution of methylamine in MeOH (200 mL) in a screw top vessel was added methyl 3-(N-carbobenzyloxyamino)-5-tert-butylthiophene-2-carboxylate (13.6 g, 39.2 mmol) and NaCN (0.98 g, 20 mmol). The vessel was sealed and the reaction mixture was heated to 50° C. for 8 h. The resulting solution was poured into water (500 mL) and extracted with EtOAc. The organic layer was washed with water and a concentrated NaCl solution, dried (Na2SO4), and concentrated under reduced pressure. The crude material was purified by flash chromatography (EtOAc/hexane) affording N-methyl-3-(N-carbobenzyloxyamino)-5-tert-butylthiophene-2-carboxamide (2.76 g, 20%).

Workup

  1. customThe vessel was sealed
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materiala concentrated NaCl solution, dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-e20e250e6cf042c88b2604b43de45d7f
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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