Ethyl isocyanate → HCID 57847093, compound

HRID 550294Notes

Reaction equation

HRID 550294 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[NH:28][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:44]([N:46]=[C:47]=[O:48])[CH3:45].O1CCCC1>O>[C:29]([NH:28][C@@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27][C@@H:22]1[C:20]([N:19]1[C@@H:15]2[C@@H:16]([C@H:7]([CH:4]3[CH2:5][CH2:6][N:1]([C:47]([NH:46][CH2:44][CH3:45])=[O:48])[CH2:2][CH2:3]3)[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[CH2:17][CH2:18]1)=[O:21])(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 57847021HCID 57847021, compound

Product 1

HCID 57847093HCID 57847093, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound (0.20 g, 0.41 mmol) synthesized in Example 69, triethylamine (0.17 g, 1.64 mmol), ethylisocyanate (0.058 g, 0.82 mmol) and tetrahydrofuran (20 ml) was stirred at room temperature for 60 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous Na2SO4), and the solvent was evaporated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (0.20 g, 87%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (over anhydrous Na2SO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-db3f0f7dc9654c469f800670a07c7ef5
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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