Pyridine → (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(2-hydroxyimino-1,1-dimethyl-ethyl)-isoxazol-5-yl]-amide

HRID 538650Notes

Reaction equation

[CH3:1][C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:13])[O:8][N:7]=1)([CH3:5])[CH:3]=O.Cl.[NH2:26][OH:27].N1C=CC=CC=1>CO>[OH:27][N:26]=[CH:3][C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:13])[O:8][N:7]=1)([CH3:1])[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To 90.0 mg (0.27 mmol) of (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-amide in MeOH (3.00 mL) are added 22.4 mg (0.32 mmol) hydroxylamine hydrochloride and 58.5 μL (0.72 mmol) pyridine. The reaction is stirred at 60° C. for 3 h. The solvent is removed under reduced pressure and the residue is purified by HPLC-MS to afford 79.0 mg of (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(2-hydroxyimino-1,1-dimethyl-ethyl)-isoxazol-5-yl]-amide. Yield: 84%; ESI-MS: 351 [M+H]+; HPLC (Rt): 1.04 min (method E)

Workup

customThe solvent is removed under reduced pressure
customthe residue is purified by HPLC-MS

Sources & evidence

ORD record: ord-d3bae2de582e448283216e4b3e1cb0ee
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865744B1

Reaction notes

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