Sodium Hydroxide → (R)-5-tert-butoxy-2-isopropoxy-7-oxiranyl-benzothiazole

HRID 1426879ノート

反応式

HRID 1426879 の反応式
[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@@H:19]([OH:22])[CH2:20]Cl)[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[N:11][C:10]=2[CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CC(OC)(C)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@@H:19]2[CH2:20][O:22]2)[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[N:11][C:10]=2[CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 86696599(R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanol

生成物 1

HCID 86696600(R)-5-tert-butoxy-2-isopropoxy-7-oxiranyl-benzothiazole収率 97.5%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 15413tert-Butyl methyl ether溶媒2 回

実験手順

To a solution of (R)-1-(5-tert-butoxy-2-isopropoxybenzo[d]thiazol-7-yl)-2-chloro-ethanol (140 g, 407.1 mmol) in TBME (420 ml) was added dropwise NaOH aqueous solution (2M, 420 ml) followed by tetrabutylammonium iodide (7.52 g, 20.36 mmol) added in one portion. After 4 h at 26° C., 400 ml TBME was added and the organic layer was separated. The aqueous layer was extracted with TBME (400 ml). The combined organic layers were washed with water (400 ml) and brine (400 ml) to give (R)-5-tert-butoxy-2-isopropoxy-7-oxiranyl-benzothiazole (122 g).

後処理

  1. additionadded in one portion
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with TBME (400 ml)
  4. washThe combined organic layers were washed with water (400 ml) and brine (400 ml)

出典と根拠

ORDレコード
ord-74fd751939b04858992343eca6cbc05e
出典データセット
uspto-grants-2015_01
特許番号
US08933108B2

反応ノート

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