Triethylamine → HCID 70227511, compound

HRID 1976354Notes

Reaction equation

HRID 1976354 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].[CH2:12]([O:19][C:20]([C:22]1[C@H:23]2[CH2:31][CH:30]=[C:29]([CH3:32])[C@@H:24]2[C@@H:25]([OH:28])[O:26][CH:27]=1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[CH2:12]([O:19][C:20]([C:22]1[C@H:23]2[CH2:31][CH:30]=[C:29]([CH3:32])[C@@H:24]2[C@H:25]([O:28][C:10](=[O:11])[NH:9][CH3:8])[O:26][CH:27]=1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 57290421HCID 57290421, compound

Product 1

HCID 70227511HCID 70227511, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9.2 ml of triethylamine and 2.4 ml of methylisocyanate were added to an acetonitrile solution containing 4.98 g of (1S,4aS,7aR)-1-hydroxy-7-methyl-1,4a,5,7a-tetrahydrocyclopenta [c]-pyrane-4-carboxylic acid benzyl ester followed by stirring for 1 hour at room temperature. The reaction mixture was then extracted with ethyl acetate. After washing the organic phase with brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless oil from the hexane-ethyl acetate eluate in the form of (1S,4aS,7aR)-7-methyl-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c]-pyrane-4-carboxylic acid benzyl ester of 5.10 g (yield: 86%). The physicochemical properties of this compound are shown below.

Workup

  1. extractionThe reaction mixture was then extracted with ethyl acetate
  2. washAfter washing the organic phase with brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-81f2fb5e4a7e40069b7155e30b1ce5f9
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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