Methyl Isocyanate → HCID 86631541, compound

HRID 659715Notes

Reaction equation

HRID 659715 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]1[NH:8][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[CH:10][N:11]=1.[CH3:30][N:31]=[C:32]=[O:33].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[CH3:30][NH:31][C:32]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[C:7]1[NH:8][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[CH:10][N:11]=1)=[O:33]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 516892Sodium BicarbonateHCID 86631540HCID 86631540, compound

Product 1

HCID 86631541HCID 86631541, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution (0.18 M) of the product from step 1 in DCM/DMF (2:1) at 0° C., methyl isocyanate (1 eq.) was added. The reaction mixture was stirred at 0° C. for 1 h. Then, NaHCO3 (saturated solution) was added and extracted with EtOAc. The combined organic layers were dried. Evaporation of the solvent gave a crude that was purified by flash chromatography on silica gel (95:5 DCM/MeOH) to yield (63%) the title compound as a solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layers were dried
  3. customEvaporation of the solvent
  4. customgave a crude that
  5. customwas purified by flash chromatography on silica gel (95:5 DCM/MeOH)

Sources & evidence

ORD record
ord-363639a7e2144140a3894992545a5785
Source dataset
uspto-grants-2011_12
Patent number
US08080573B2

Reaction notes

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