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

HRID 1426879Notes

Reaction equation

HRID 1426879 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-74fd751939b04858992343eca6cbc05e
Source dataset
uspto-grants-2015_01
Patent number
US08933108B2

Reaction notes

Loading…