Water → HCID 10764583, compound

HRID 1736251Notes

Reaction equation

HRID 1736251 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:20])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([F:19])[CH:13]=3)[O:11][C:6]=2[C:5]([F:21])=[C:4]([CH2:22][OH:23])[C:3]=1[F:24].Cl[C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27].O>N1C=CC=CC=1>[CH2:29]([O:28][C:26]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[O:11][C:6]3[C:5]([F:21])=[C:4]([CH2:22][OH:23])[C:3]([F:24])=[C:2]([NH2:1])[C:7]=3[C:8](=[O:20])[CH:9]=2)=[CH:13][C:14]=1[F:19])=[O:27])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 962WaterHCID 18052Allyl chloroformateHCID 10735574HCID 10735574, compound

Product 1

HCID 10764583HCID 10764583, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.72 mg (20.0 mmol) of Compound 118 obtained in Example 118 was dissolved in 200 mL of pyridine, 10.6 mL (100 mmol) of allyl chloroformate was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction solution and the precipitated crystals were collected by filtration. The crystals were dissolved in 500 mL of ethanol, 18 mL of a 2N aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction solution and the precipitated crystals were collected by filtration, to give 6.92 g of Compound P (yield: 82%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. dissolutionThe crystals were dissolved in 500 mL of ethanol
  4. addition18 mL of a 2N aqueous solution of sodium hydroxide was added
  5. stirringthe mixture was stirred at room temperature for 1.5 hours
  6. additionWater was added to the reaction solution
  7. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-03e272969fef493ba074e320f33b4d45
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

Loading…