Pyridine → 7-Acetyl-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl benzyl carbonate

HRID 749245Notes

Reaction equation

HRID 749245 reaction equation
[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.C(Cl)Cl.O>[C:29](=[O:30])([O:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:14][C:7]1[C:8]2[NH:9][C:10](=[O:13])[S:11][C:12]=2[C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 450769877-Acetyl-4-hydroxybenzo[d]thiazol-2(3H)-one

Product 1

HCID 693156917-Acetyl-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl benzyl carbonate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 7-acetyl-4-hydroxy-1,3-benzothiazol-2(3H)-one (209 mg) in dry THF (5 ml) and DCM (5 ml) with pyridine (0.2 ml), stirring under nitrogen, was cooled to −10° C. and benzylchloroformate (0.37 mls) was added. After 18 h stirring at room temperature, the mixture was diluted with water and extracted into DCM. The solution was dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with a stepped gradient of 25% to 100% ethyl acetate-cyclohexane mixtures, to give the title compound (280 mg). LCMS RT=3.19 min.

Workup

  1. stirringAfter 18 h stirring at room temperature
  2. extractionextracted into DCM
  3. dry with materialThe solution was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified on a 10 g silica SPE cartridge
  7. washeluting with a stepped gradient of 25% to 100% ethyl acetate-cyclohexane mixtures

Sources & evidence

ORD record
ord-24e2d05433524b74b856148bc5f5f3b3
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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