Triethylamine → 4-(4-methylpentanoyl)-2-(R)-(2-(R)-acetylamino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436512
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:27])[C@H:15]([NH:23][C:24](=[O:26])[CH3:25])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][CH:29]([CH3:35])[CH2:30][CH2:31][C:32](O)=[O:33].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:32](=[O:33])[CH2:31][CH2:30][CH:29]([CH3:35])[CH3:28])[CH2:10][C@@H:9]1[C@@H:14]([OH:27])[C@H:15]([NH:23][C:24](=[O:26])[CH3:25])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 12587Isocaproic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 690153032-(R)-(2-(R)-Acetylamino-1-(S)-hydroxy-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 690190384-(4-methylpentanoyl)-2-(R)-(2-(R)-acetylamino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dissolve 2-(R)-(2-(R)-Acetylamino-1-(S)-hydroxy-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester (122 mg, 0.32 mmol) in 3 ml of dry CH2Cl2. Add 4-methylpentanoic acid (0.04 ml, 0.32 mmol), EDCI (73.6 mg, 0.38 mmol), HOBT (51.8 mg, 0.38 mmol), triethylamine (0.13 ml, 0.96 mmol) and dimethylaminopyridine (3.9 mg, 0.032 mmol), and stir at room temperature overnight. Dilute with CH2Cl2, and wash with 5% NaHCO3 followed by saturated aqueous sodium chloride. Dry organic layer with MgSO4 and remove the solvent under reduced pressure. Subject residue to silica gel chromatography, eluting with ethyl acetate/methanol 9:1 to obtain 74 mg (48% yield) of a white solid.

Aufarbeitung

  1. washwash with 5% NaHCO3
  2. customDry organic layer with MgSO4 and remove the solvent under reduced pressure
  3. washSubject residue to silica gel chromatography, eluting with ethyl acetate/methanol 9:1

Quellen und Nachweise

ORD-Eintrag
ord-c23312a64101455e90e53e3a972f1aa8
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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