Acetonitrile → HCID 57124693, compound

HRID 1976356Notes

Reaction equation

HRID 1976356 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].C(#N)C.[CH3:15][O:16][C:17]([C:19]1[C@H:20]2[CH2:28][C@@H:27]3[O:29][C@:26]3([CH3:30])[C@@H:21]2[CH:22]([OH:25])[O:23][CH:24]=1)=[O:18]>CO>[CH3:15][O:16][C:17]([C:19]1[C@H:20]2[CH2:28][C@@H:27]3[O:29][C@:26]3([CH3:30])[C@@H:21]2[C@H:22]([O:25][C:10](=[O:11])[NH:9][CH3:8])[O:23][CH:24]=1)=[O:18]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 57213576HCID 57213576, compound

Product 1

HCID 57124693HCID 57124693, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.15 ml of triethylamine and 60 μl of methylisocyanate were added to an acetonitrile solution containing 200 mg of a known (4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta [c] pyrane-4-carboxylic acid methylester followed by stirring for 1 hour at room temperature. After adding 1 ml of methanol to the reaction mixture, it was concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain colorless needles from the hexane-ether eluate in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-methylcarbamoyloxy-7-methylcyclopenta [c] pyrane-4-carboxylic acid methylester (55 mg, yield : 22%). The physicochemical properties of this compound are described in Table 1, Compound No. 3).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ca60f2227d9f42b995c9384cb3c45ef2
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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