Sulfuric Acid → HCID 19434887, compound

HRID 1736185Notes

Reaction equation

HRID 1736185 reaction equation
[F:1][C:2]1[C:3]([CH2:35][OH:36])=[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:37](=O)(=[O:40])([OH:39])[OH:38]>>[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][S:37]([OH:40])(=[O:39])=[O:38])[C:2]=1[F:1]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 10673123HCID 10673123, compound

Product 1

HCID 19434887HCID 19434887, compoundYield 36%

Conditions

Temperature
50 °C

Procedure

10 mL of concentrated sulfuric acid was added to 1.00 g (1.98 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-hydroxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 118 (4) and the mixture was stirred at 50° C. for 20 minutes. The reaction solution was cooled on ice, ice water was added and the precipitated crystals were collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:methanol=9:1-chloroform:methanol:aqueous ammonia=40:10:1) and triturated with ethanol to give 293 mg of Compound 119 (yield: 36%).

Workup

  1. additionwas added
  2. filtrationthe precipitated crystals were collected by filtration
  3. customThe crystals were purified by silica gel column chromatography (chloroform:methanol=9:1-chloroform:methanol:aqueous ammonia=40:10:1)
  4. customtriturated with ethanol

Sources & evidence

ORD record
ord-e89f4379550e4308989dbf4cd8bb233d
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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