Acetic Acid → (4S)-1-{[(3S,4R)-1-(aminocarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide

HRID 1361336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361336
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][CH2:10][C@H:9]2[C:13]([N:15]2[CH2:24][C@@H:23]([N:25]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:22][C@H:16]2[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[O:14])=[CH:4][CH:3]=1.[O:40]([C:42]#[N:43])[K].C(O)(=O)C>CN(C=O)C>[NH2:43][C:42]([N:11]1[CH2:12][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C@H:9]([C:13]([N:15]2[CH2:24][C@@H:23]([N:25]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:22][C@H:16]2[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[O:14])[CH2:10]1)=[O:40]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 24826348(4S)-1-[(3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamideHCID 178418250HCID 178418250, Verbindung

Produkt 1

HCID 24826432(4S)-1-{[(3S,4R)-1-(aminocarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (4S)-1-{[(3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide (84 mg, 0.15 mmol) prepared in Example E1-1 in DMF was added dropwise KOCN (24 mg, 0.3 mmol) and a catalytic amount of acetic acid. The reaction mixture was stirred at rt for 1 h, extracted with EtOAc, washed with excessive amount of water and brine, and the organic solution was dried over MgSO4. The residue was purified by HPLC to give the title compound.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washwashed with excessive amount of water and brine
  3. dry with materialthe organic solution was dried over MgSO4
  4. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c3d965994f86430688c5234a41f1b268
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879852B2

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