Hydrochloric Acid → 1-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

HRID 1942711ノート

反応式

HRID 1942711 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:32][CH3:33])=[C:19]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([O:30]C)=[O:29])[CH2:25]4)[CH:20]=[CH:21][CH:22]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>O1CCCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:32][CH3:33])=[C:19]([CH2:23][N:24]4[CH2:25][CH:26]([C:28]([OH:30])=[O:29])[CH2:27]4)[CH:20]=[CH:21][CH:22]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58494145HCID 58494145、化合物

生成物 1

HCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid収率 105.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylate (D13) (30.3 g, 62.3 mmol) in Tetrahydrofuran (THF) (200 mL), Ethanol (150 mL) and Water (60 mL) was added sodium hydroxide (4.99 g, 125 mmol). The reaction mixture was stirred at room temperature overnight. Then pH of the reaction mixture was adjusted with 6 N HCl until pH ˜2.0. White solid was precipitated. The organic solvent was removed in by rotary evaporator. The solid was collected through filtration. The solid was washed water (150 mL×3) and dried in vacuo to afford 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3 azetidinecarboxylic acid (31 g), which was used for the following procedure without further purification.

後処理

  1. customWhite solid was precipitated
  2. customThe organic solvent was removed in by rotary evaporator
  3. filtrationThe solid was collected through filtration
  4. washThe solid was washed water (150 mL×3)
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-9929a74fd5ce47bdb220a735333595b2
出典データセット
uspto-grants-2013_03
特許番号
US08389508B2

反応ノート

読み込み中…