4-Toluenesulfonyl chloride → [(4R/S)-3-Fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

HRID 15120

反応式

HRID 15120 の反応式
[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][C:8](=[O:17])[N:9]3[CH2:13][C:12]([OH:16])([CH2:14][OH:15])[C:11]=1[C:10]=23.FC1C=NC2C=CC(=O)N3CC(=C)C=1C=23.C(N(CC)CC)C.[C:40]1([CH3:50])[CH:45]=[CH:44][C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1.C([Sn](=O)CCCC)CCC>ClCCl.O1CCCC1.CN(C)C=O.O>[CH3:50][C:40]1[CH:45]=[CH:44][C:43]([S:46]([O:15][CH2:14][C:12]2([OH:16])[C:11]3=[C:2]([F:1])[CH:3]=[N:4][C:5]4[CH:6]=[CH:7][C:8](=[O:17])[N:9]([C:10]=43)[CH2:13]2)(=[O:48])=[O:47])=[CH:42][CH:41]=1

参加物

8

反応物 5

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 61221Dibutyltin oxideHCID 23634273(4R/S)-3-fluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneHCID 675275493-Fluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

生成物 1

HCID 131728163[(4R/S)-3-Fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 86642945dichloromethane tetrahydrofuran DMF溶媒

実験手順

A mixture of (4R/S)-3-fluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (553 mg, 2.3 mmol) (racemic material, prepared from 3-fluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one using AD mix alpha/beta in a similar manner to Example 1(e) Method A) in dichloromethane/tetrahydrofuran/N,N-dimethylformamide (19 ml19 ml/2 ml) was treated with triethylamine (0.5 ml, 3.5 mmol), para-toluenesulphonyl chloride (446 mg, 2.3 mmol) and dibutyltin oxide (29 mg, 0.1 mmol) and stirred at room temperature overnight. Water was then added, the organic phase was separated and washed with saturated aqueous sodium bicarbonate, separated, dried over magnesium sulphate and evaporated under vacuum. The residue was chromatographed on silica eluting with 0-100% ethyl acetate in dichloromethane then 0-10% methanol in ethyl acetate affording a white solid (321 mg, 35%).

後処理

  1. customthe organic phase was separated
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customseparated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on silica eluting with 0-100% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-90c35ecce929460ca5f37a3bf5782e19
出典データセット
uspto-grants-2010_06
特許番号
US07732460B2

関連ノート

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