2-(Benzenesulfonyl)-3-phenyloxaziridine → (8-Cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester

HRID 586548ノート

反応式

HRID 586548 の反応式
[CH2:1]([O:8][C:9](=[O:30])[NH:10][CH2:11][C:12]1[C:23](=[O:24])[N:22]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:15]2[N:16]=[C:17]([S:20][CH3:21])[N:18]=[CH:19][C:14]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:38])C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9](=[O:30])[NH:10][CH2:11][C:12]1[C:23](=[O:24])[N:22]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:15]2[N:16]=[C:17]([S:20]([CH3:21])=[O:38])[N:18]=[CH:19][C:14]=2[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 69208844(8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester

生成物 1

HCID 69206663(8-Cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester収率 56.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester (1.67 g, 3.93 mmol) and 2-benzenesulfonyl-3-phenyl-oxaziridine (1.34 g, 5.11 mmol) were dissolved in dichloromethane (20 mL) and stirred at ambient temperature for 12 hours. The reaction mixture was then purified by silica gel chromatography to give (8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester as a white solid (0.98 g, 56.6%). 1H NMR δ (400 MHz, CDCl3) 8.89 (s, 1H), 7.68 (s, 1H), 7.32 (m, 5H), 5.96 (m, 1H), 5.52 (t, J=6.4 Hz, 1H), 5.09 (s, 2H), 4.32 (d, J=6.3 Hz, 2H), 2.95 (s, 3H), 2.22 (m, 2H), 2.12 (m, 2H), 1.95 (m, 2H), 1.69 (m, 2H).

後処理

  1. customThe reaction mixture was then purified by silica gel chromatography

出典と根拠

ORDレコード
ord-39c24c71fb3c4e1fa1e606ca74fd8393
出典データセット
uspto-grants-2005_08
特許番号
US06936612B2

反応ノート

読み込み中…