Diethyl Ether → Isopropyl 3-[2-chloro-4-fluoro-5-(tetrahydro-1,3,7-trioxo-1H-imidazo [5,1-c][1,4]thiazin-2(3H)-yl) phenyl]tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 1474

反応式

HRID 1474 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:17](=[O:18])[CH:12]3[CH2:13][S:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[CH:4][C:3]=1[N:20]1[C:25](=[O:26])[N:24]([CH3:27])[C:23](=[O:28])[N:22]([CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[C:21]1=[O:36].I([O-])(=O)(=O)=[O:38].[Na+].CCOCC>CO.O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:17](=[O:18])[CH:12]3[CH2:13][S:14](=[O:38])[CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[CH:4][C:3]=1[N:20]1[C:25](=[O:26])[N:24]([CH3:27])[C:23](=[O:28])[N:22]([CH2:29][C:30]([O:32][CH:33]([CH3:34])[CH3:35])=[O:31])[C:21]1=[O:36]

参加物

7

反応物 3

HCID 3283Diethyl EtherHCID 23667635Sodium periodateHCID 67713947isopropyl 3-{2-chloro-4-fluoro-5-[5,6,8,8a-tetrahydro-1,3-dioxo-1H-imidazo [5,1-c][1,4]-thiazin-2(3H)-yl]phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

生成物 1

HCID 19690723Isopropyl 3-[2-chloro-4-fluoro-5-(tetrahydro-1,3,7-trioxo-1H-imidazo [5,1-c][1,4]thiazin-2(3H)-yl) phenyl]tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate収率 60.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

A mixture of isopropyl 3-{2-chloro-4-fluoro-5-[5,6,8,8a-tetrahydro-1,3-dioxo-1H-imidazo[5,1-c][1,4]-thiazin-2(3H)-yl]phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.95 g, 1.75 mmol) in methanol (10 mL) is added over 15 minutes to a solution of sodium periodate (0.38 g, 1.78 mmol) in water (10 mL) which is previously cooled to 0°-5° C. After the addition is complete, the reaction mixture is stirred at room temperature overnight, diluted with methylene chloride, washed sequentially with a one molar KH2PO4 solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow foam. Flash column chromatography of the foam using silica gel, a 10% ether in methylene chloride solution and a 2.5% methanol in methylene chloride solution gives the title product as a white foam (0.59 g, mp 175°-180° C.).

後処理

  1. temperatureis previously cooled to 0°-5° C
  2. additionAfter the addition
  3. washwashed sequentially with a one molar KH2PO4 solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow foam

出典と根拠

ORDレコード
ord-9c45683f083c467ebf79ecae3d3dc9a0
出典データセット
uspto-grants-1998_03
特許番号
US05726126

関連ノート

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