Sodium ethoxide → HCID 68426676, compound

HRID 642569Notes

Reaction equation

HRID 642569 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][S:13][CH:14]([CH3:16])[CH3:15])[C:9]2[N:17]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[S:19][C:8]=2[C:7]=1[O:24]C(=O)C(C)(C)C)=[O:5])[CH3:2].[O-]CC.[Na+]>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][S:13][CH:14]([CH3:15])[CH3:16])[C:9]2[N:17]=[C:18]([C:20]([CH3:22])([CH3:21])[CH3:23])[S:19][C:8]=2[C:7]=1[OH:24])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 68428603HCID 68428603, compound

Product 1

HCID 68426676HCID 68426676, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-tert-butyl-7-(2,2-dimethyl-propionyloxy)-4-isopropylsulfanylmethyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (150 mg, 0.33 mmol) and sodium ethoxide (215 mg of 21% sodium ethoxide in ethanol) in 0.6 mL of ethanol was heated at 90° C. for 2 h. The reaction mixture was diluted with ethyl acetate and washed with 1 N HCl and brine. The organic fraction was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography, eluting the desired product from silica gel with a gradient of 0-40% ethyl acetate in hexanes to give 80 mg of a clear oil. MS (ESI+): m/z 368.9 (M+1).

Workup

  1. washwashed with 1 N HCl and brine
  2. dry with materialThe organic fraction was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography
  5. washeluting the desired product from silica gel with a gradient of 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-415b20728188477d91427136b294cfce
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…