Phenyl isocyanate → HCID 69848506, compound

HRID 352245Notes

Reaction equation

HRID 352245 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:20]([CH3:23])[O:21][N:22]=3)[C:6](=[O:19])[N:7]([C@H:12]3[CH2:17][CH2:16][CH2:15][C@@H:14]([NH2:18])[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+].[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:20]([CH3:23])[O:21][N:22]=3)[C:6](=[O:19])[N:7]([C@H:12]3[CH2:17][CH2:16][CH2:15][C@@H:14]([NH:18][C:33]([NH:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:34])[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 69848396HCID 69848396, compound

Product 1

HCID 69848506HCID 69848506, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the suspension of cis-1-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-3-amino-cyclohexane (0.0446 g, 0.121 mmol) in 1 mL anhydrous THF at RT was added 2N NaOH (0.60 mL, 0.121 mmol). After 5 min. the phenylisocyanate (0.013 mL,0.121 mmol). After 20 min. the reaction was diluted with EtOAc, washed with water and concentrated to near dryness. After sonication and filtration a white solid (0.0412, 75%) was obtained.

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. customAfter sonication and filtration a white solid (0.0412, 75%)
  4. customwas obtained

Sources & evidence

ORD record
ord-cd980476296d4ba1a6434152dc8e95e2
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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