Methyl 2-isocyanato-2-methylpropanoate → HCID 10276449, compound

HRID 2306088Notes

Reaction equation

HRID 2306088 reaction equation
[CH2:1]([O:8][NH:9][C@@H:10]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH2:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]([C:25]([CH3:31])([CH3:30])[C:26](OC)=[O:27])=[C:23]=[O:24]>C1COCC1>[CH2:1]([O:8][NH:9][C@@H:10]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH2:11][N:12]1[C:26](=[O:27])[C:25]([CH3:31])([CH3:30])[NH:22][C:23]1=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2769374Methyl 2-isocyanato-2-methylpropanoateHCID 9968310HCID 9968310, compound

Product 1

HCID 10276449HCID 10276449, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 3G (19.7 g) in THF (100 mL) at room temperature was treated with the solution of the methyl 2-isocyanato-2-methylpropanoate in THF, stirred for 25 minutes, and concentrated to a volume of 170 mL. The concentrate was treated with THF (80 mL) and 6M HCl (95 mL), heated to reflux, stirred for 6 hours, cooled to room temperature, concentrated, and extracted with isopropyl acetate. The extract was washed sequentially with water, saturated NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated to provide 24.2 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ8.33 (s, 1H), 7.47 (m, 2H), 7.35 (m, 5H), 6.90 (m, 2H), 6.78 (d, 1H, J=5 Hz), 4.65 (m, 2H), 4.00 (m, 2H), 3.68 (m, 1H), 3.55 (m, 2H), 1.30 (s, 3H), 1.28 (s, 3H).

Workup

  1. concentrationconcentrated to a volume of 170 mL
  2. additionThe concentrate was treated with THF (80 mL) and 6M HCl (95 mL)
  3. temperatureheated
  4. temperatureto reflux
  5. stirringstirred for 6 hours
  6. concentrationconcentrated
  7. extractionextracted with isopropyl acetate
  8. washThe extract was washed sequentially with water, saturated NaHCO3, and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-106bce5e6cd2470da9c90c3891608ad6
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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