Pyridine → HCID 10198383, compound

HRID 915334Notes

Reaction equation

HRID 915334 reaction equation
CN(C=O)C.C(Cl)(=O)C(Cl)=O.[O:12]=[C:13]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([NH2:28])=O)[C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH2:16][CH3:17].N1C=CC=CC=1>C(#N)C.O>[O:12]=[C:13]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]#[N:28])[C:14](=[O:20])[C:15]([CH3:18])([CH3:19])[CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 9794760HCID 9794760, compound

Product 1

HCID 10198383HCID 10198383, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 0.465 mL DMF (6 mmol) in 10 mL acetonitrile at 0° C. was added 0.48 mL (5.5 mmol) of oxalyl chloride. A white precipitate formed immediately and was accompanied by gas evolution. When complete, a solution of 1.2 g (5 mmol) of (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxamide (from Example 2) in 2.5 mL acetonitrile was added. When the mixture became homogeneous, 0.9 mL (11 mmol) pyridine was added. After 5 min., the mixture was diluted into water and extracted by 200 mL ethyl acetate. The organic layer was concentrated and further purified by silica gel to give 0.8 g product as a white solid (72% yield). 1H NMR (CDCl3): δ 0.87 (t, 0.3H, J=7.5); 1.22 (s, 3H); 1.24 (s, 3H); 1.80 (m, 2H); 2.03–2.23 (m, 4H); 3.55 (m, 2H); 4.73 (m, 1H).

Workup

  1. customA white precipitate 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-ca3cd5b08df54accb59ba00a5da65aba
Source dataset
uspto-grants-2007_09
Patent number
US07265150B1

Reaction notes

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