Triacetoxyperiodinane → 8-Fluoro-3-oxo-4-(2-oxoethyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide

HRID 558959Notes

Reaction equation

HRID 558959 reaction equation
[CH3:1][C:2]1[CH:26]=[C:25]([C:27]([N:29]2[CH2:35][CH2:34][CH2:33][CH2:32][C:31]3[CH:36]=[CH:37][CH:38]=[CH:39][C:30]2=3)=[O:28])[CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[F:18])[N:11]([CH2:19][CH2:20][OH:21])[C:10](=[O:22])[CH2:9]1)=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:1][C:2]1[CH:26]=[C:25]([C:27]([N:29]2[CH2:35][CH2:34][CH2:33][CH2:32][C:31]3[CH:36]=[CH:37][CH:38]=[CH:39][C:30]2=3)=[O:28])[CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[F:18])[N:11]([CH2:19][CH:20]=[O:21])[C:10](=[O:22])[CH2:9]1)=[O:7]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 115482588-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide

Product 1

HCID 115338268-Fluoro-3-oxo-4-(2-oxoethyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylamide from Example 9 (105 mg, 0.20 mmol) in dichloromethane (5 ml) was added Dess-Martin periodinane (100 mg, 0.24 mg). The mixture was stirred for 2 h and evaporated. The residue was taken up in chloroform and water and separated. The organic layer was dried and evaporated. The residue was purified by flash chromatography on silica (eluant methanol:dichloromethane 4:96) to give a white solid; yield 73 mg, 69%.

Workup

  1. customevaporated
  2. customwater and separated
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica (eluant methanol:dichloromethane 4:96)
  6. customto give a white solid

Sources & evidence

ORD record
ord-4cec32232e0c435b9517a04fff59cd4a
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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