Hydrochloric Acid → HCID 15896176, compound

HRID 1857796Notes

Reaction equation

HRID 1857796 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]1[C:13](=[O:14])[C:12]2[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][C:17]([CH2:19][OH:20])=[N:18][C:11]=2[O:10][CH2:9][CH2:8]1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=[O:39].Cl>S([O-])([O-])(=O)=S.[Na+].[Na+]>[F:35][C:2]([F:1])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]1[C:13](=[O:14])[C:12]2[C:15]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:16][C:17]([C:19]([OH:39])=[O:20])=[N:18][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24401PermanganateHCID 15896175HCID 15896175, compound

Product 1

HCID 15896176HCID 15896176, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 24477Sodium ThiosulfateSolvent

Procedure

A mixture of 4-[3,5-bis(trifluoromethyl)benzyl]-8-hydroxymethyl-2,3,4,5-tetrahydro-5-oxo-6-phenylpyrido[3,2-f][1,4]oxazepine (Example 55) (3.49 g), 2N-NaOH (100 ml) and pottasium permanganate (2.22 g) was stirred for 45 hours at room temperature. To the reaction mixture was added saturated aqueous sodium thiosulfate (10 ml). After the pH of the mixture was adjusted to ca.3 using hydrochloric acid. The mixture was extracted with ethyl acetate-THF (1:2). The extract was washed with aqueous sodium chloride solution, dried and evaporated to give the entitled compound as colorless crystals (2.74 g). m.p. 119-123° C. (recrystallized from methanol-ethyl ether) NMR(200 MHz, DMSO-d6) ppm: 3.94(2H,b), 4.46(2H,b), 4.91(2H,s), 7.25-7.55(5H,m), 7.90(1H,s), 8.06(2H,s), 8.12(1H,s).

Workup

  1. extractionThe mixture was extracted with ethyl acetate-THF (1:2)
  2. washThe extract was washed with aqueous sodium chloride solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-bff703587cb0411bb859fa39f5f4d6a4
Source dataset
uspto-grants-2000_11
Patent number
US06147071

Reaction notes

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