Benzyl Alcohol → HCID 59375144、化合物

HRID 661970ノート

反応式

HRID 661970 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12](C(O)=O)[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C1(P([N:41]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:44]1([CH2:50][OH:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[O:52]1[CH2:57]COCC1>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([NH:41][C:57](=[O:52])[O:51][CH2:50][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2]

参加物

5

反応物 4

HCID 244Benzyl AlcoholHCID 312751,4-DioxaneHCID 199401P,P-Diphenylphosphinic azideHCID 59375023HCID 59375023、化合物

生成物 1

HCID 59375144HCID 59375144、化合物収率 83%

反応条件

温度
50 °C

実験手順

A suspension of 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylic acid (Example 23-2, 320 mg, 0.919 mmol) and 4 Å molecular sieves (60 mg) in 1,4-dioxane (15 mL) at 50° C. was treated with TEA (0.316 mL, 2.269 mmol) and diphenylphosphoryl azide (0.491 mL, 2.269 mmol). The mixture was stirred at 50° C. for 1.5 h, followed by addition of phenylmethanol (0.951 mL, 9.19 mmol). The mixture was then stirred at 80° C. for 18 h. The cooled mixture was partitioned between EtOAc and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated The residue was purified by column chromatography (eluting with 35:65 hexane-EtOAc). The residue after concentration was suspended in hexane and the precipitate was collected by filtration to provide benzyl 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-ylcarbamate as an off-white solid (400 mg, 83%). 1H NMR (400 MHz, DMSO-d6) δ 11.50 (s, 1H) 9.83 (s, 1H) 8.15 (br. s., 1H) 8.00 (s, 1H) 7.91 (d, J=7.69 Hz, 1H) 7.45-7.64 (m, 3H) 7.32-7.46 (m, 7H) 7.03 (d, J=7.91 Hz, 1H) 6.87-6.98 (m, 2H) 5.15 (s, 2H). Mass spectrum m/z 454.1 (M+H)+.

後処理

  1. stirringThe mixture was then stirred at 80° C. for 18 h
  2. customThe cooled mixture was partitioned between EtOAc and NaHCO3 (aq)
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated The residue
  6. customwas purified by column chromatography (eluting with 35:65 hexane-EtOAc)
  7. concentrationThe residue after concentration
  8. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-59fa0b33bd0c4fbab08b3b6315aeeab2
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

反応ノート

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