Ethyl isocyanate → HCID 71279055, compound

HRID 2171052Notes

Reaction equation

HRID 2171052 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[O:16][CH2:15]2.Br[CH2:23][C:24]1([CH2:28][OH:29])[CH2:27][O:26][CH2:25]1.C([O-])([O-])=O.[K+].[K+].[CH2:36]([N:38]=[C:39]=[O:40])[CH3:37]>CN(C=O)C.C(N(CC)CC)C.O>[CH3:9][O:8][C:7]1[C:6]([O:10][CH3:11])=[CH:5][CH:4]=[C:3]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[O:16][CH2:15]3)[C:2]=1[O:1][CH2:23][C:24]1([CH2:28][O:29][C:39](=[O:40])[NH:38][CH2:36][CH3:37])[CH2:27][O:26][CH2:25]1

Participants

8

Reactant 4

HCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 529264[3-(Bromomethyl)oxetan-3-yl]methanolHCID 67461726HCID 67461726, compound

Product 1

HCID 71279055HCID 71279055, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

In a screw cap vessel Compound 306 (0.017 g, 0.06 mmol) and 3-bromomethyl-3-hydroxymethyl-oxetane (0.22 g, 0.12 mmol) were dissolved in DMF (0.5 mL) and K2CO3 (0.02 g, 0.15 mmol) was added. The suspension was heated at 100° C. for 3 h. H2O (3 mL) was added and the suspension was extracted with EtOAc (3×3 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. In a screw cap vessel the crude product was dissolved in CH3CN (0.2 mL). Triethyl amine (0.003 mL) and Ethyl isocyanate (0.044 mL, 0.6 mmol) were added. The mixture was heated at 50° C. for 18 h and the solvent was evaporated. The crude product was purified by flash chromatography using toluene:EOAc 60:40->40:60 as the eluent. This afforded the title compound as an oil.

Workup

  1. extractionthe suspension was extracted with EtOAc (3×3 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customIn a screw cap vessel the crude product
  7. dissolutionwas dissolved in CH3CN (0.2 mL)
  8. temperatureThe mixture was heated at 50° C. for 18 h
  9. customthe solvent was evaporated
  10. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-355e5e85196a4c75bacef0b614878d34
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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