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

HRID 15126

反応式

HRID 15126 の反応式
[Cl: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.C(N(CC)CC)C.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.O>ClCCl.O1CCCC1.CN(C)C=O.C([Sn](=O)CCCC)CCC>[CH3:35][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O:15][CH2:14][C:12]2([OH:16])[C:11]3=[C:2]([Cl: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:33])=[O:32])=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23633411(4R/S)-3-Chloro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

生成物 1

HCID 131728164(4R/S)-(3-chloro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl 4-methylbenzenesulfonate収率 95.2%

試薬・触媒・溶媒 2

HCID 61221Dibutyltin oxide触媒HCID 86642945dichloromethane tetrahydrofuran DMF溶媒

実験手順

A suspension of (4R/S)-3-chloro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (300 mg, 1.2 mmol) in dichloromethane/tetrahydrofuran/N,N-dimethylformamide (10 ml/10 ml/2 ml) was treated with triethylamine (0.25 ml, 1.8 mmol), para-toluenesulphonyl chloride (220 mg, 1.2 mol) and dibutyltin oxide (15 mg, 0.06 mmol). After 3 hours water was added and the phases separated. The organic phase was washed with saturated aqueous sodium bicarbonate solution then dried and evaporated affording the product (465 mg).

後処理

  1. customthe phases separated
  2. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution
  3. customthen dried
  4. customevaporated

出典と根拠

ORDレコード
ord-67728f421e3f4195ad806ed49d11f5d7
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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