Acetic Anhydride → 1-acetyl-6-chloro-4'-[5-chloro-2-(1-ethyl-1-methanesufonylaminocarbonyl-propoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 658924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658924
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:45])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH2:34][CH3:35])([C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[CH2:25][CH3:26])[CH2:14][C:13](=[O:36])[NH:12][CH:11]3[C:37]3[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=3[CH3:44])[C:5]2=[CH:4][CH:3]=1.[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:46]([N:8]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=3[O:23][C:24]([CH2:34][CH3:35])([C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[CH2:25][CH3:26])[CH2:14][C:13](=[O:36])[NH:12][CH:11]2[C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[CH3:44])[C:9]1=[O:45])(=[O:48])[CH3:47]

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 749286676-chloro-4'-[5-chloro-2-(1-ethyl-1-methanesulfonylaminocarbonyl-propoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Produkt 1

HCID 667698831-acetyl-6-chloro-4'-[5-chloro-2-(1-ethyl-1-methanesufonylaminocarbonyl-propoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 23,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At room temperature, to a mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-2-(1-ethyl-1-methanesulfonylaminocarbonyl-propoxy)-phenyl]-2′-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (400 mg, 0.58 mmol) and acetic anhydride (71 mg, 0.69 mmol) in DCM (20 mL) was added DMAP (7 mg, 0.06 mmol) slowly. After the mixture was stirred for 2 h, the solution was washed by 0.5N HCl solution twice, dried over anhydrous Na2SO4 and concentrated. The residue was purified by Prep-HPLC to give the title compound as a white solid (100 mg).

Aufarbeitung

  1. washthe solution was washed by 0.5N HCl solution twice
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by Prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f1be3584a2d146a3b4c2d04cf68f55a0
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076482B2

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