Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol

HRID 1468682Notes

Reaction equation

HRID 1468682 reaction equation
C([O:7][CH2:8][C@@H:9]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:10]1[C:18]([CH3:19])=[CH:17][C:13]2[N:14]=[CH:15][S:16][C:12]=2[C:11]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)(=O)C(C)(C)C.[OH-].[Na+]>CO.C1COCC1.C(OCC)(=O)C>[C:28]([O:27][C@@H:9]([C:10]1[C:18]([CH3:19])=[CH:17][C:13]2[N:14]=[CH:15][S:16][C:12]=2[C:11]=1[C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:8][OH:7])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 70980986(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

Product 1

HCID 70981123(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate (5J) (8 mg, 0.0174 mmol) in MeOH (0.5 mL) and THF (1 mL) was added sodium hydroxide (2 M, 0.1 mL, 0.2 mmol) and the reaction mixture was stirred at room temperature overnight. Reaction mixture diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. Aqueous layer back-extracted with ethyl acetate and combined organic layer was dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C20H22ClNO2S: 376.1 (M+H+). Found: 376.1 (M+H+).

Workup

  1. customReaction mixture
  2. washwashed with saturated sodium bicarbonate solution
  3. extractionAqueous layer back-extracted with ethyl acetate and combined organic layer
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3ff53a9010a144fdb5d7d91607726e7e
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

Loading…