Acetic Acid → HCID 22310861, Verbindung

HRID 2305588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305588
C([BH3-])#N.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:20]([O:22][CH3:23])=[O:21].[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=O.C(O)(=O)C>CO>[Cl:5][C:6]1[CH:7]=[C:8]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH2:29][C:28]([O:32][CH2:33][CH3:34])=[O:31])=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:20]([O:22][CH3:23])=[O:21]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydrideHCID 22310882HCID 22310882, Verbindung

Produkt 1

HCID 22310861HCID 22310861, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (0.2 g) was added in a single portion to methyl N-(3,4-dichlorobenzyl)-5-aminoindole-2-carboxylate (0.16 g), ethyl glyoxalate (0.2 ml of 50 wt % solution in toluene) and acetic acid (0.1 ml) in methanol (3 ml). The reaction was stirred for 5 mins then partitioned between ethyl acetate and 2M HCl. Combined organic extracts were dried (MgSO4) and concentrated to give an oil which crystallised upon trituration with i-hexane. Filtration yielded the desired end product as an off-white powder (0.136 g, 67%); NMR δ(CD3SOCD3) 1.18 (t, 3H), 3.79 (s, 3H), 3.82 (d, 2H), 4.08 (q, 2H), 5.72 (s, 2H), 6.60-7.50 (m, 7H); M/z (+) 435 (M+), 133.

Aufarbeitung

  1. customthen partitioned between ethyl acetate and 2M HCl
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil which
  5. customcrystallised upon trituration with i-hexane
  6. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-189944261a8b4d7f892a7c249c2d8f8f
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441004B1

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