Pyridine → HCID 15231547, compound

HRID 1081481Notes

Reaction equation

HRID 1081481 reaction equation
[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=3[O:28][CH3:29])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].[CH2:32]([CH:34]([CH2:38][CH3:39])[C:35](Cl)=[O:36])[CH3:33].N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:35](=[O:36])[CH:34]([CH2:38][CH3:39])[CH2:32][CH3:33])=[CH:23][C:22]=3[O:28][CH3:29])(=[O:19])=[O:20])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 759542-Ethylbutyryl chlorideHCID 15231545HCID 15231545, compound

Product 1

HCID 15231547HCID 15231547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g of the compound obtained in Example 5 step B) in 20 ml of DCM was mixed with 0.5 g of 2-ethylbutyroyl chloride and 0.5 g of pyridine. The mixture was concentrated under vacuum, extracted with ethyl ether and then washed with water, with 1N hydrochloric acid and then with water. The residue was chromatographed on silica using DCM as the eluent to give the expected product, which crystallized from isopropyl ether. m=0.17 g. M.p.=168° C.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. extractionextracted with ethyl ether
  3. washwashed with water, with 1N hydrochloric acid
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-c24a0fa503fe4058881299ccf75dee7d
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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