Ethyl isocyanate → HCID 57860052, compound

HRID 1947141Notes

Reaction equation

HRID 1947141 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].C1COCC1.[CH2:41]([N:43]=[C:44]=[O:45])[CH3:42]>C(OCC)(=O)C>[CH2:41]([NH:43][C:44]([N:33]1[CH2:32][CH2:31][CH:30]([NH:29][C:27]([C:4]2[N:5]([CH3:26])[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH2:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:8](=[O:25])[C:7]=3[C:3]=2[O:2][CH3:1])=[O:28])[CH2:35][CH2:34]1)=[O:45])[CH3:42]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 57860479HCID 57860479, compound

Product 1

HCID 57860052HCID 57860052, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the compound of Example 77 (200 mg, 0.423 mmol) and THF (10 mL) was added ethyl isocyanate (101 μL, 1.27 mmol) at 0° C., and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate). Recrystallization of the obtained solid from ethyl acetate-THF gave the title compound (172 mg, 75%) as a white powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate)
  5. customRecrystallization of the obtained solid from ethyl acetate-THF

Sources & evidence

ORD record
ord-7d7e40460b2c4418a4d80f7a1fa32460
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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