Pyridine → HCID 86745883, compound

HRID 892617Notes

Reaction equation

HRID 892617 reaction equation
[O:1]=[C:2]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:3][CH2:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C@H:8]1[CH:9]=O)=[O:6].Cl.[NH2:24][OH:25].N1C=CC=CC=1>CN(C=O)C>[O:1]=[C:2]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:3][CH2:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C@H:8]1[CH:9]=[N:24][OH:25])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 9797271N-(4-Chloro-benzyl)-4-((S)-2-formyl-pyrrolidin-1-yl)-4-oxo-butyramide

Product 1

HCID 86745883HCID 86745883, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-[4-oxo-4-(4-chlorobenzylamino)butanoyl]-L-prolinal (304 mg) in DMF (2.5 ml) were added hydroxylamine hydrochloride (75 mg) and pyridine (90 μl), and the mixture was stirred at 70° C. for 2 hours. To a solution of crude (2S)-1-[4-oxo-4-(4-chlorobenzylamino)butanoyl]-2-pyrrolidinecarboxaldehyde oxime as obtained by subjecting the reaction mixture to concentration under reduced pressure, in methylene chloride (4 ml) were added pyridine (0.16 ml) and acetic anhydride (0.19 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was treated in the same manner as in Example 15 to give 249 mg of (2S)-1-[4-oxo-4-(4-chlorobenzylamino)butanoyl]-2-pyrrolidinecarboxaldehyde O-acetyloxime.

Sources & evidence

ORD record
ord-2aa19b9a5a1446e198e48850a51d4958
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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