Sodium Methoxide → (S)-2-(7-bromo-2-methoxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

HRID 1468711Notes

Reaction equation

HRID 1468711 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20](Cl)[S:21][C:17]=2[C:16]=1[Br:26])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:27][O-:28].[Na+]>CO>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20]([O:28][CH3:27])[S:21][C:17]=2[C:16]=1[Br:26])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 70981474(S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Product 1

HCID 70982393(S)-2-(7-bromo-2-methoxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalateYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The reaction mixture of (S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (65I) (90 mg, 0.195 mmol), NaOMe in MeOH (25% wt, 66 ul) in MeOH (3 ml) was heated at 50° C. for 20 min in sealed microwave vial. The reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in Hexanes to give 65J (70 mg, 79%).

Workup

  1. washThe reaction mixture was washed by sat. NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down
  6. custompurified by silica gel column
  7. washeluting by 0-100% EtOAc in Hexanes

Sources & evidence

ORD record
ord-ed3393ae7e744afc9436623fd058edfa
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

Loading…