HCID 19434964, compound → HCID 10643350, compound

HRID 1736225Notes

Reaction equation

HRID 1736225 reaction equation
[F:1][C:2]1[C:3]([CH2:35][O:36][CH2:37][CH2:38][CH3:39])=[C:4]([F:34])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)C(C)(C)C)=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27]C(=O)C(C)(C)C>S(=O)(=O)(O)O>[NH2:27][C:26]1[C:6]2[C:7](=[O:25])[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([F:24])[CH:12]=3)[O:10][C:5]=2[C:4]([F:34])=[C:3]([CH2:35][O:36][CH2:37][CH2:38][CH3:39])[C:2]=1[F:1]

Participants

3

Reactant 1

HCID 19434964HCID 19434964, compound

Product 1

HCID 10643350HCID 10643350, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

The above 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-7-propyloxymethyl-4H-1-benzopyran-4-one was dissolved in 30 mL of a 50% aqueous solution of sulfuric acid, and the solution was stirred at 100° C. for 15 minutes. Then, the mixture was poured into ice-water and neutralized. The precipitate was collected and purified by silica gel column chromatography (chloroform:methanol=100:1) followed by recrystallization from ethyl acetate/n-hexane, to give 286 mg of Compound 150 (yield: 76%).

Workup

  1. customThe precipitate was collected
  2. custompurified by silica gel column chromatography (chloroform:methanol=100:1)
  3. customfollowed by recrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9d2f1f0011814bb192915ac449675860
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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