Perchloric Acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

HRID 1468681Notes

Reaction equation

HRID 1468681 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:11]1[C:19]([CH3:20])=[CH:18][C:14]2[N:15]=[CH:16][S:17][C:13]=2[C:12]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[OH:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:1]([O:7][CH2:8][C@@H:9]([O:10][C:2]([CH3:4])([CH3:3])[CH3:1])[C:11]1[C:19]([CH3:20])=[CH:18][C:14]2[N:15]=[CH:16][S:17][C:13]=2[C:12]=1[C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 70981222(S)-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyethyl pivalate

Product 1

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

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A solution of (S)-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyethyl pivalate (5I) (0.016 g, 0.040 mmol) and perchloric acid, 70% (6 μl, 0.1 mmol) in tert-butyl acetate (1 mL) was stirred at room temperature for 2 h. Reaction mixture was quenched with solid sodium bicarbonate (0.05 g) for 1 h. Saturated sodium bicarbonate solution was added and extracted with ethyl acetate (3×). The 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 C25H30ClNO3S: 460.2 (M+H+). Found: 460.2 (M+H+).

Workup

  1. customReaction mixture
  2. customwas quenched with solid sodium bicarbonate (0.05 g) for 1 h
  3. additionSaturated sodium bicarbonate solution was added
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-81b1b8ff33a94f49b8fbc713292b456e
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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