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

Reaktionsgleichung

Reaktionsgleichung von HRID 15126
[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

Komponenten

7

Edukt 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

Produkt 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-methylbenzenesulfonateAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 61221Dibutyltin oxideKatalysatorHCID 86642945dichloromethane tetrahydrofuran DMFLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-67728f421e3f4195ad806ed49d11f5d7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732460B2

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