Hydrochloric Acid → 1-benzyloxycarbonylmethyl-3-(1-carboxy-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 482724

Reaktionsgleichung

Reaktionsgleichung von HRID 482724
C([BH3-])#N.[Na+].[CH2:5]([O:12][C:13]([CH2:15][N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][CH2:19][CH:18]([NH2:27])[C:17]1=[O:28])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:29]([CH2:36][C:37](=O)[C:38]([OH:40])=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>CO>[CH2:5]([O:12][C:13]([CH2:15][N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][CH2:19][CH:18]([NH:27][CH:37]([C:38]([OH:40])=[O:39])[CH2:36][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:17]1=[O:28])=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 697322-Oxo-4-phenylbutyric acid2×HCID 5003444Sodium cyanoborohydrideHCID 132434981-benzyloxycarbonylmethyl-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Produkt 1

HCID 202447451-benzyloxycarbonylmethyl-3-(1-carboxy-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (0.152 g, 0.0014 mol) was added to a solution of 1-benzyloxycarbonylmethyl-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (0.45 g, 0.0014 mol) and benzylpyruvic acid (0.48 g, 0.0028 mol) in methanol (35 ml). The reaction mixture was stirred at room temperature under nitrogen for 2 hours. Additional benzylpyruvic acid (0.48 g, 0.0028 mol) was added, and the reaction mixture stirred for an additional 18 hours. Concentrated hydrochloric acid (0.5 ml) was added and the resulting solution stirred for 1 hour. The solvents were removed under reduced pressure and the residue treated with dichloromethane (100 ml) to precipitate sodium chloride. After filtration, the solvent was removed under reduced pressure and the residue chromatographed on silica gel (30 g). Elution with ethyl acetate/methanol/acetic acid (90:10:0.2) gave 1-benzyloxycarbonylmethyl-3-(1-carboxy-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one as an oil; NMR(CDCl3) 7.35(m,14H), 5.10(s, 2H), 4.60(m,2H), 3.00(m, 12H).

Aufarbeitung

  1. stirringthe reaction mixture stirred for an additional 18 hours
  2. stirringthe resulting solution stirred for 1 hour
  3. customThe solvents were removed under reduced pressure
  4. additionthe residue treated with dichloromethane (100 ml)
  5. customto precipitate sodium chloride
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue chromatographed on silica gel (30 g)
  9. washElution with ethyl acetate/methanol/acetic acid (90:10:0.2)

Quellen und Nachweise

ORD-Eintrag
ord-6bc87c84813341f68d209f5e8c741faa
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04575503

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