Pyridine → HCID 9794936, compound

HRID 2373309Notes

Reaction equation

HRID 2373309 reaction equation
CN(C=O)C.C(Cl)(=O)C(Cl)=O.[C:12]1([CH2:18][S:19]([N:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[C:27]([NH2:29])=O)(=[O:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>C(#N)C.O>[C:12]1([CH2:18][S:19]([N:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[C:27]#[N:29])(=[O:20])=[O:21])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9795374HCID 9795374, compound

Product 1

HCID 9794936HCID 9794936, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 0.67 ml DMF (8.7 mmol) in 10 ml acetonitrile at 0° C. was added 0.70 ml (8.0 mmol) oxalyl chloride. A white precipitate was formed immediately and was accompanied by gas evolution. When complete, a solution of 2.0 g (7.5 mmol) of (2S)-1-(phenylmethyl)sulfonyl-2-pyrrolidinecarboxamide in 5.0 ml acetonitrile was added. When the mixture became homogeneous, 1.35 ml (16.5 mmol) pyridine was added. After 5 min., the mixture was diluted with water, and extracted by 200 ml ethyl acetate. The organic layer was concentrated and further purified by silica gel to give 1.5 g product as a white solid (80% yield). 1H NMR (CDCl3): d 01.92 (m, 2H); 2.01 (m, 1H); 2.11 (m, 1H); 3.45 (m, 2H); 4.35 (s, 2H); 4.65 (m, 1H); 7.26-7.45 (m, 5H, aromatic).

Workup

  1. customA white precipitate was formed immediately
  2. extractionextracted by 200 ml ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customfurther purified by silica gel

Sources & evidence

ORD record
ord-26b1542fd0004a4f85b6cecb6e649401
Source dataset
uspto-grants-2008_12
Patent number
US07459473B2

Reaction notes

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