Ethyl isocyanate → HCID 86656352, compound

HRID 1942475Notes

Reaction equation

HRID 1942475 reaction equation
[OH:1][CH2:2][C:3]1([CH3:40])[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]2[CH:16]=[C:17]([C:21]([N:23]([CH:37]([CH3:39])[CH3:38])[C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]3)=[O:22])[C:18]([CH3:20])=[CH:19][C:5]=2[O:4]1.[CH2:41]([N:43]=[C:44]=[O:45])[CH3:42]>O1CCCC1>[CH2:41]([NH:43][C:44]([O:1][CH2:2][C:3]1([CH3:40])[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]2[CH:16]=[C:17]([C:21]([N:23]([CH:37]([CH3:38])[CH3:39])[C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:25]3)=[O:22])[C:18]([CH3:20])=[CH:19][C:5]=2[O:4]1)=[O:45])[CH3:42]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 67329605HCID 67329605, compound

Product 1

HCID 86656352HCID 86656352, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (3R)-3-[{[2-(hydroxymethyl)-4-(4-methoxybutyl)-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (66 mg) in tetrahydrofuran (1 ml) was added ethyl isocyanate (83 mg), and the mixture was stirred at 60° C. for 4 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (65 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fa0a0451a63e4287bc0ca6c15be0152c
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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