Ethyl isocyanate → HCID 59806015, compound

HRID 1661508Notes

Reaction equation

HRID 1661508 reaction equation
O[C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:29]=[CH:28][C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20]C(=O)OC(C)(C)C)=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31].C(C(CCCC)C([O-])=[O:39])C.[Sn+2].C(C(CCCC)C([O-])=O)C>ClCCl.C(O)(C(F)(F)F)=O>[CH2:30]([NH:32][C:33](=[O:39])[O:34][C@H:6]1[CH2:2][CH2:3][N:4]([C:7]2[CH:29]=[CH:28][C:10]([C:11](=[O:12])[NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH2:20])=[CH:9][CH:8]=2)[CH2:5]1)[CH3:31]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 93182-ethylhexanoic acid tin(II) saltHCID 58417043HCID 58417043, compound

Product 1

HCID 59806015HCID 59806015, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 161 (100 mg, 0.25 mmol) and ethyl isocyanate (29 μL, 28 mg, 0.375 mmol) in dichloromethane (5 mL) was treated with tin(II) 2-ethylhexanoate (44 μL, 55 mg, 0.135 mmol). The reaction mixture was stirred overnight at r.t. under nitrogen, concentrated and the residue was purified by flash chromatography using gradient 70 to 90% EtOAc in hexanes as an eluent. The material obtained was then dissolved in 2:1 mixture of dichloromethane and TFA (3 mL), stirred for 30 min and concentrated. The residue was then dissolved in EtOAc (5 mL) and washed with saturated NaHCO3 solution (5 mL), dried over Na2SO4, filtered and concentrated to afford title compound 162 (39 mg, 42% yield). 1H NMR: CDCl3 δ(ppm): 7.7 (d J=8.8 Hz, 2H), 7.6 (s, 1H), 7.2 (d, J=7.6 Hz, 1H), 7.0 (t, J=8.8 Hz, 1H), 6.8 (t, J=7.8 Hz, 2H), 6.5 (d, J=8.8 Hz, 2H), 5.3 (s, 1H), 4.6 (s, 1H), 3.9 (s, 2H), 3.6 (m, 1H), 3.4 (m, 3H), 3.1 (m, 2H), 2.2 (m, 2H), 1.2 (s, 1H), 1.1 (m, 3H). LRMS (ESI): (calc) 368.18 (found) 369.1 (MH+).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by flash chromatography
  3. customThe material obtained
  4. stirringstirred for 30 min
  5. concentrationconcentrated
  6. dissolutionThe residue was then dissolved in EtOAc (5 mL)
  7. washwashed with saturated NaHCO3 solution (5 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-772ba4ea9430458dabf386edd35c3076
Source dataset
uspto-grants-2011_10
Patent number
US08030344B2

Reaction notes

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