1,1-Dichloroethane → HCID 178465325, compound

HRID 1007973Notes

Reaction equation

HRID 1007973 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].C(N([CH2:11][CH3:12])CC)C.[CH2:13]([NH:20][C@H:21]1[CH2:26][CH2:25][C@@H:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][Si](C(C)(C)C)(C)C)=[CH:29][C:28]=2[O:41][Si](C(C)(C)C)(C)C)[CH2:23][CH2:22]1)[C:14]1C=CC=[CH:16][CH:15]=1.Cl[CH:50](Cl)C>>[CH2:13]([N:20]([C@H:21]1[CH2:22][CH2:23][C@@H:24]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]=2[OH:41])[CH2:25][CH2:26]1)[C:4]([NH:3][CH2:1][CH3:2])=[O:5])[C:14]1[CH:12]=[CH:11][CH:50]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 178455053HCID 178455053, compound

Product 1

HCID 178465325HCID 178465325, compoundYield 19%

Conditions

Temperature
80 °C

Procedure

A solution of ethylisocyanate (0.038 ml, 0.48 mmol), triethylamine (0.065 ml) and cis-N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]amine (0.122 g) in dichloroethane (10 ml) was stirred at room temperature for 60 hr. The reaction mixture was partitioned between water (10 ml) and dichloromethane (10 ml). The aqueous layer was separated and extracted with dichloromethane (2×10 ml) and the combined organic extracts washed with brine (10 ml), dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was dissolved in dichloromethane (15 ml) and warmed with a mixture of water (7.5 ml) and trifluoroacetic acid (7.5 ml) at 80° C. for 17 hr. Toluene (25 ml) was then added and the mixture concentrated in vacuo. Methanol (25 ml) was then added and the mixture again concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether) afforded the title compound (0.016 g, 19%) as a colourless solid. δH (CD3OD) 1.08 (3H, t), 1.57-1.88 (6H, m), 2.12 (2H, m), 3.16 (1H, m), 3.24 (2H, m), 4.17 (1H, m), 4.52 (2H, s), 6.09 (1H, t), 6.24 (1H, dd), 6.29 (1H, d), 6.98 (1H, d) and 7.22-7.37 (5H, m). m/s(ES+) 369.54 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water (10 ml) and dichloromethane (10 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (2×10 ml)
  4. washthe combined organic extracts washed with brine (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. dissolutionThe resulting residue was dissolved in dichloromethane (15 ml)
  9. additionToluene (25 ml) was then added
  10. concentrationthe mixture concentrated in vacuo
  11. additionMethanol (25 ml) was then added
  12. concentrationthe mixture again concentrated in vacuo
  13. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-fd2bc5ae440f42dc84034b5daae45810
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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