Hydrochloric Acid → HCID 10601101, compound

HRID 1736162Notes

Reaction equation

HRID 1736162 reaction equation
[N:1]([C:4]1[C:28]([F:29])=[C:27]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]2[C:8](=[O:26])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([F:25])[CH:13]=3)[O:11][C:6]=2[C:5]=1[F:37])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[OH-].[Na+]>O1CCCC1>[NH2:1][C:4]1[C:28]([F:29])=[C:27]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]2[C:8](=[O:26])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([F:25])[CH:13]=3)[O:11][C:6]=2[C:5]=1[F:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 10649513HCID 10649513, compound

Product 1

HCID 10601101HCID 10601101, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.50 g (6.80mmol) of 7-azido-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 93 (1) was suspended in 120 mL of tetrahydrofuran, 1.96 g (7.48 mmol) of triphenylphosphine was added and the mixture was stirred at room temperature for 2 hours. To this was added 50 mL of 1N hydrochloric acid and the mixture was further stirred for 10 hours. The mixture was adjusted to pH 9 by addition of a 10N aqueous solution of sodium hydroxide thereto, and the precipitated crystals were collected by filtration and purified by silica gel column chromatography (chloroform-chloroform:methanol=40:l) to give 2.83 g of 7-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one (yield: 85%).

Workup

  1. stirringthe mixture was further stirred for 10 hours
  2. filtrationthe precipitated crystals were collected by filtration
  3. custompurified by silica gel column chromatography (chloroform-chloroform:methanol=40:l)

Sources & evidence

ORD record
ord-e4b54beef80a44638109e91a845aa598
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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