Sulfuric Acid → HCID 10365608, compound

HRID 1736192Notes

Reaction equation

HRID 1736192 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.[C:37](O)(=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].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][C:37](=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:2]=1[F:1]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 8892Hexanoic AcidHCID 10673123HCID 10673123, compound

Product 1

HCID 10365608HCID 10365608, compoundYield 55%

Procedure

Substantially the same manner as that in Example 123 was repeated except that 1.06 g (2.10 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-hydroxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 118 (4), 24 mL of hexanoic acid and 6 mL of concentrated sulfuric acid were used, and the resulting compound was purified by silica gel column chromatography (chloroform:acetonitrile=30:1-20:1) and recrystallized from ethyl acetate/n-hexane, to give 489 mg of Compound 125 (yield: 55%).

Workup

  1. customthe resulting compound was purified by silica gel column chromatography (chloroform:acetonitrile=30:1-20:1)
  2. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-28fe8e6229b440df96e7e5c5fc21ba5f
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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