Thionyl Chloride → HCID 68426440, compound

HRID 642559Notes

Reaction equation

HRID 642559 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:11](CC2C=CC(OC)=CC=2OC)[CH2:10][C:9]2[N:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[S:25][C:8]=2[C:7]1=[O:30])=[O:5])[CH3:2].S(Cl)(Cl)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[S:25][C:8]=2[C:7]=1[OH:30])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68426445HCID 68426445, compound

Product 1

HCID 68426440HCID 68426440, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-tert-butyl-5-(2,4-dimethoxy-benzyl)-7-oxo-4,5,6,7-tetrahydro-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (1 g, 2.3 mmol) in 23 mL of dichloromethane was cooled to 0° C. with an external ice bath and thionyl chloride (253 μL, 3.47 mmol) was added. The ice bath was removed and the reaction was allowed to stir at room temperature for 16 h. Pyridine (500 μL) was added and the mixture was stirred for 5 min before concentrating on silica gel under reduced pressure and purification by column chromatography. The desired product was eluted from silica gel with a gradient of 10-50% ethyl acetate in hexanes to give 363 mg of pale yellow solid. MS (ESI−): m/z 279.3 (M−1).

Workup

  1. customThe ice bath was removed
  2. additionPyridine (500 μL) was added
  3. stirringthe mixture was stirred for 5 min
  4. concentrationbefore concentrating on silica gel under reduced pressure and purification by column chromatography
  5. washThe desired product was eluted from silica gel with a gradient of 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-72cec0cc5ff44732abd6545746785669
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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