Water → (5R)-2-[(2S)-2-(3,4-dichlorophenyl)4-oxobutyl]-1-oxo-1,2,3,4-tetrahydronaphtho[1,2-f][1,4]thiazepine-6-carbonitrile 5-oxide

HRID 1760955Notes

Reaction equation

HRID 1760955 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:29][CH:30]=C)[CH2:10][N:11]2[C:17](=[O:18])[C:16]3[C:19]4[C:24]([CH:25]=[C:26]([C:27]#[N:28])[C:15]=3[S:14][CH2:13][CH2:12]2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:5]=[CH:6][C:7]=1[Cl:8].C1COCC1.[OH2:37].I([O-])(=O)(=O)=O.[Na+].[OH2:44]>[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:29][CH:30]=[O:44])[CH2:10][N:11]2[C:17](=[O:18])[C:16]3[C:19]4[C:24]([CH:25]=[C:26]([C:27]#[N:28])[C:15]=3[S@:14](=[O:37])[CH2:13][CH2:12]2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 98046052-[(2S)-2-(3,4-Dichlorophenyl)pent-4-enyl]-1-oxo-1,2,3,4-tetrahydronaphtho[1,2-f][1,4]thiazepine-6-carbonitrileHCID 21881883Oxolane--water (1/1)HCID 23667635Sodium periodate

Product 1

HCID 86759590(5R)-2-[(2S)-2-(3,4-dichlorophenyl)4-oxobutyl]-1-oxo-1,2,3,4-tetrahydronaphtho[1,2-f][1,4]thiazepine-6-carbonitrile 5-oxide

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 2-[(2S)-2-(3,4-dichlorophenyl)pent-4-enyl]-1-oxo-1,2,3,4-tetrahydronaphtho[1,2-f][1,4]thiazepine-6-carbonitrile (Example 1, 225 mg, 0.50 mmol) in 3:1 THF/water (10 mL) under nitrogen at 0° C. was added osmium tetroxide (4% in water, 32.5 μL, 0.01 mmol) followed in 10 min by portion wise addition of sodium periodate over 5 min. The reaction mixture was allowed to warm to ambient temperature over 3 h and clarified by the addition of water. The products were extracted into ether and organic layer was washed with saturated NaHCO3 and brine, dried (Na2SO4), and evaporated to 230 mg of an oil which was chromatographed on silica gel in 10% MeOH/CHCl3 to give 40 mg of intermediate 78a, 22 mg of Intermediate 78b and 11 mg of Intermediate 78c.

Workup

  1. extractionThe products were extracted into ether and organic layer
  2. washwas washed with saturated NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to 230 mg of an oil which
  5. customwas chromatographed on silica gel in 10% MeOH/CHCl3

Sources & evidence

ORD record
ord-3d3d2235f68f41f4aaaaf576293135dc
Source dataset
uspto-grants-2005_01
Patent number
US06846814B2

Reaction notes

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