Dichloromethane → (S)-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyethyl pivalate

HRID 1468680Notes

Reaction equation

HRID 1468680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[S:15][CH:14]=[N:13][C:12]=3[CH:11]=[C:10]([CH3:17])[C:9]=2[C@H:18]([OH:21])[CH2:19][OH:20])=[CH:4][CH:3]=1.ClCCl.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>N1C=CC=CC=1.C(OCC)(=O)C>[C:27]([O:20][CH2:19][C@H:18]([C:9]1[C:10]([CH3:17])=[CH:11][C:12]2[N:13]=[CH:14][S:15][C:16]=2[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[OH:21])(=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 62493Pivaloyl chloride3×HCID 70981470(S)-1-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethane-1,2-diol

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethane-1,2-diol (5H) (0.018 g, 0.056 mmol) in pyridine (0.5 mL)/dichloromethane (1 mL) was added trimethylacetyl chloride (0.010 mL, 0.081 mmol). Reaction mixture was stirred for 1 h at room temperature and additional trimethylacetyl chloride (0.020 ml 0.081 mmol) was added and left it overnight at room temperature. More trimethylacetyl chloride (0.030 ml, 0.242 mmol) was added to the mixture and stirred at room temperature for 30 min. Reaction mixture was diluted with ethyl acetate. Organic layer was washed with saturated sodium bicarbonate solution, dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C21H22ClNO3S: 404.1 (M+H+). Found: 404.1 (M+H+).

Workup

  1. customReaction mixture
  2. waitleft it overnight at room temperature
  3. stirringstirred at room temperature for 30 min
  4. customReaction mixture
  5. washOrganic layer was washed with saturated sodium bicarbonate solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-858e2dcf6b5d4fa4921a8019223805ad
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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