Pyridine → HCID 131718969, compound

HRID 1654536Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]=O)=[O:19])=[O:12].Cl.[NH2:28][OH:29].N1C=CC=CC=1>CN(C)C=O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]=[N:28][OH:29])=[O:19])=[O:12]

Participants

Conditions

Temperature: 70 °C

Procedure

1-[3-(Indan-2-ylacetyl)-L-thioprolyl]-L-prolinal (372 mg), hydroxylamine hydrochloride salt (76 mg) and pyridine (89 μl) were dissolved in 5 ml of dimethylformamide, and stirred at 70° C. for 1.5 hours. After concentrating the reaction solution under reduced pressure, the resulting residue was dissolved in 30 ml of methylene chloride, washed by saturated aqueous sodium chloride solution, and dried over magnesium sulfate, followed by distillation of the solvent under reduced pressure. The resulting residue was purified by column chromatography to obtain 120 mg of (2S)-1-[3-(indan-2-ylacetyl)-L-thioprolyl]-2-pyrrolidine aldoxime. Yield; 31%.

Workup

concentrationAfter concentrating the reaction solution under reduced pressure
dissolutionthe resulting residue was dissolved in 30 ml of methylene chloride
washwashed by saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
distillationfollowed by distillation of the solvent under reduced pressure
customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record: ord-444b58cd211e450fa1774fb1b71daf6a
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05407950

Reaction notes

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