Phenyl isocyanate → HCID 13911555, compound

HRID 653400Notes

Reaction equation

HRID 653400 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][N+:7]([O-])=[O:8].[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][C:6]1[CH2:13][CH:12]([C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[O:8][N:7]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 25604Methyl 4-nitrobutyrate

Product 1

HCID 13911555HCID 13911555, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 105 g of 4-nitrobutyric acid methyl ester (Bruson U.S. Pat. No. 2,342,119), 64 g of t-butyl acrylate, 1 ml triethyl amine in 200 ml of toluene is stirred and treated dropwise with 137 g of phenyl isocyanate. The mixture is stirred for 72 hours at room temperature and heated at 90° C. for two hours. The mixture is cooled, filtered to remove the diphenyl urea, and concentrated under reduced pressure. The resulting oil is chromatographed on elution with hexane:ethyl-acetate; 75:25) to yield 4,5-dihydro 5-(t-butoxycarbonyl)-3-isoxazolepropanoic acid methyl ester as a colorless oil. NMR (CDCl3) and 4.87 (t, J=9 Hz, 1H), 3.70 (s, 3H), 3.20 (d, J=9 Hz, 2HO, 2.67 (s, 4H), 1.47 (s, 9H). IR (cm-1) 2970, 1740, 1600, 1556, 1445, 1396, 1373, 1340, 1300, 1262, 1230.

Workup

  1. temperatureheated at 90° C. for two hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customto remove the diphenyl urea
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil is chromatographed on elution with hexane

Sources & evidence

ORD record
ord-3a08ea5d5ef546a2b4a90999fba2b495
Source dataset
uspto-grants-1987_06
Patent number
US04677098

Reaction notes

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