Tetrahydrofuran → HCID 178452623、化合物

HRID 1064202ノート

反応式

HRID 1064202 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=C)[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].[O:25]1CCCC1.C([O-])([O-])=O.[K+].[K+].I([O-])(=O)(=O)=O.[Na+]>C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[O:25])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 23667635Sodium periodateHCID 136141708(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 178452623HCID 178452623、化合物収率 22%

試薬・触媒・溶媒 2

HCID 962Water溶媒4 回HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of the title compound of Example 164 (48 mg, 0.146 mmol) in 1:1 tetrahydrofuran:H2O (4 mL) was added K2CO3 (30 mg, 0.219 mmol), K2OSO2(OH)4 (7 mg) and K3Fe(CN)6 (72 mg, 0.219 mmol). The mixture was stirred at room temperature for 2 hours whereupon water and ethyl acetate were added. Following extractive work-up, the organic layer was then dried, filtered, and concentrated. The residue was dissolved in 1:1 tetrahydrofuran:H2O (2 mL) and sodium periodate (156 mg, 50.73 mmol) was added. The mixture was stirred at room temperature for 30 min whereupon water and ethyl acetate were added. Following extractive work-up, the organic layer was then dried, filtered, and concentrated. Silica gel chromatography of the residue, eluting with 30% ethyl acetate in hexane gave Intermediate 230(a) as a pale yellow solid (11 mg, 0.034 mmol) in 22% yield.

後処理

  1. additionwere added
  2. customthe organic layer was then dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 1:1 tetrahydrofuran
  6. additionwere added
  7. customthe organic layer was then dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography of the residue, eluting with 30% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-860dcb08235e4f73a959542eeb555b76
出典データセット
uspto-grants-2005_11
特許番号
US06967198B2

反応ノート

読み込み中…