Sodium hydride → HCID 58573862, compound

HRID 932294Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[C@@H:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[NH:14][C:13](=[O:23])[C@:12]([CH2:25][C:26]([O:28][CH3:29])=[O:27])([CH3:24])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[N+:30](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C=O)C>[NH2:30][N:14]1[C@H:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C@@H:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)[CH2:11][C@@:12]([CH2:25][C:26]([O:28][CH3:29])=[O:27])([CH3:24])[C:13]1=[O:23]

Participants

Conditions

Temperature: 23 °C

Procedure

A suspension of 60% sodium hydride in mineral oil (0.953 g, 23.82 mmol) was added to solution of methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetate (Example 429, step A, 4.84 g, 11.9 mmol) in DMF (25 mL). The resulting mixture was stirred for 15 min at 23° C. O-(2,4-dinitrophenyl)hydroxylamine (4.74 g, 23.82 mmol) was added at room temperature. The solution was stirred for 1 h at room temperature then quenched with MeOH (1 mL). Excess solvent was removed under reduced pressure and the residue was purified by chromatography on silica (eluent: 0 to 5% MeOH in DCM; stepwise gradient) to give the title compound.

Workup

stirringThe solution was stirred for 1 h at room temperature
customthen quenched with MeOH (1 mL)
customExcess solvent was removed under reduced pressure
customthe residue was purified by chromatography on silica (eluent

Sources & evidence

ORD record: ord-1dd8c00c757c4b40b0fd80c1c5de28d8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296736B2

Reaction notes

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