HCID 136344431, compound → HCID 86705044, compound

HRID 1427253Notes

Reaction equation

HRID 1427253 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:18]2[C:26]3[C:21](=[C:22]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)([CH2:16][CH3:17])[C:9]([NH:11][C:12](=[N:14]O)[CH3:13])=[O:10])=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:18]2[C:26]3[C:21](=[C:22]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)([C:9]2[O:10][N:14]=[C:12]([CH3:13])[N:11]=2)[CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 136344431HCID 136344431, compound

Product 1

HCID 86705044HCID 86705044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-chlorophenyl)-N-(1-(hydroxyimino)ethyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanamide (148 mg, 0.32 mmol) in THF (5 mL) was heated at 70° C. for 2 days. Then the solvent was removed in vacuo to afford the crude product. The product was purified by column chromatography (50% EtOAc/hexanes), then by chiral separation following the conditions below provided the title compound as a single enantiomer.

Workup

  1. customThen the solvent was removed in vacuo
  2. customto afford the crude product
  3. customThe product was purified by column chromatography (50% EtOAc/hexanes)
  4. customby chiral separation

Sources & evidence

ORD record
ord-7b9e6a4220764e44aad18949198fc9c8
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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