Isocyanate → Methyl 3-{[(N-Methylcarbamoyl)methylthio]methyl}-4-oxo-4-(3-pyridyl)butanoate

HRID 2184729Notes

Reaction equation

HRID 2184729 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9](=[CH2:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:8])[CH:2]=1.[CH3:16][NH:17][C:18](=[O:21])[CH2:19][SH:20].[N-]=C=O>ClCCl.C(N(CC)CC)C>[CH3:16][NH:17][C:18]([CH2:19][S:20][CH2:15][CH:9]([C:7](=[O:8])[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:21]

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 4047279Acetamide, 2-mercapto-N-methyl-HCID 22457736Methyl 3-(3-Pyridylcarbonyl)but-3-enoate

Product 1

HCID 22457729Methyl 3-{[(N-Methylcarbamoyl)methylthio]methyl}-4-oxo-4-(3-pyridyl)butanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of methyl 3-(3-pyridylcarbonyl)but-3-enoate in dichloromethane (0.5 mL, 0.1 mM), triethylamine in dichloromethane (0.5 mL, 0.1 mM) and N-methyl-2-sulfanylacetamide (0.6 mL, 0.12 mmol) was stirred for 24 h. PS isocyanate resin (60 mg) was added to the reaction mixture and stirred for 24 h. The solution was filtered and concentrated to give the title compound in quantitative yield, ESMS, (M+1)+311.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-97fe9f0aa32c4e15b247125eab8ce31c
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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