2,4,6-Trimethylpyridine → (RS)-ethoxy-(2-oxo-3-phenylmethanesulfonylamino-2H-pyridin-1-yl)-acetic acid ethyl ester

HRID 1828095Notes

Reaction equation

HRID 1828095 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]1=[O:16])[O:6][CH2:7][CH3:8])[CH3:2].N1C(C)=CC(C)=CC=1C.[C:27]1([CH2:33][S:34](Cl)(=[O:36])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:6][CH2:7][CH3:8])[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:34]([CH2:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:36])=[O:35])[C:10]1=[O:16])[CH3:2]

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 69641593(RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester

Product 1

HCID 69641458(RS)-ethoxy-(2-oxo-3-phenylmethanesulfonylamino-2H-pyridin-1-yl)-acetic acid ethyl esterYield 84.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution (RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester (428 mg) and 2,4,6-collidine (0.47 ml) in THF (3 ml) under an argon atmosphere was added dropwise a solution of alpha-toluenesulphonylchloride (340 mg) in THF (2 ml) over 10 min. When addition was complete, stirring at 0° C. was continued for 2 h. The mixture was diluted with EtOAc, washed with 1.0 N HCl and brine, dried (MgSO4), filtered and concentrated to give (RS)-ethoxy-(2-oxo-3-phenylmethanesulfonylamino-2H-pyridin-1-yl)-acetic acid ethyl ester (592 mg) as light brown solid. MS 393.0 ([M−H]−)

Workup

  1. additionWhen addition
  2. washwashed with 1.0 N HCl and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-58ba4278dc084ec689e6fd4f7f8b661b
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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