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

HRID 1426879노트

반응식

HRID 1426879 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 15413tert-Butyl methyl ether용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-74fd751939b04858992343eca6cbc05e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933108B2

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