Ammonium Chloride → HCID 75985813, Verbindung

HRID 417295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417295
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[NH:12][C:13]([CH:15]1[NH:19][CH:18]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]2([C:32]3[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=3)[NH:26][C:25]2=[O:34])[CH:16]1[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=1[F:42])=[O:14].[NH4+].[Cl-]>CO.[Zn]>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([NH:12][C:13]([CH:15]2[NH:19][CH:18]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]3([C:32]4[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=4)[NH:26][C:25]3=[O:34])[CH:16]2[C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=2[F:42])=[O:14])=[C:3]([O:2][CH3:1])[CH:8]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 75985747rac-(2'S,3'R,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid (2-methoxy-4-nitro-phenyl)-amide

Produkt 1

HCID 75985813HCID 75985813, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid (2-methoxy-4-nitro-phenyl)-amide (35 mg, 0.057 mmol) in methanol (3 mL) was added an aqueous solution (1.5 mL) of NH4Cl (30 mg, 0.57 mmol), followed by activated Zinc (Aldrich, 37 mg, 0.57 mmol). The reaction mixture was stirred at room temperature for 0.5 h. The mixture was filtered through a short pad of celite. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (0-50% EtOAc in dichloromethane) to give rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid (4-amino-2-methoxy-phenyl)-amide as a off white solid (24 mg, 72%).

Aufarbeitung

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe mixture was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionaqueous layer was extracted with ethyl acetate
  6. extractionThe combined organic extract
  7. washwas washed with water, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography (0-50% EtOAc in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-5b7c827fa8a04669939aac4fd3c1b2e0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088815B2

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