Triethylamine → ethyl 2-{[5-(benzyloxy)-N-(tert-butoxycarbonyl)-L-norvalyl]amino}-3-oxobutanoate

HRID 869700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869700
C1(NC2CCCCC2)CCCCC1.[C:14]([O:18][C:19]([NH:21][CH:22]([CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]([OH:25])=O)=[O:20])([CH3:17])([CH3:16])[CH3:15].[NH2:37][CH:38]([C:44](=[O:46])[CH3:45])[C:39]([O:41][CH2:42][CH3:43])=[O:40].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(OCC)(=O)C.CO.C(Cl)(Cl)Cl.O>[CH2:30]([O:29][CH2:28][CH2:27][CH2:26][C@@H:22]([C:23]([NH:37][CH:38]([C:44](=[O:46])[CH3:45])[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:25])[NH:21][C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:20])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

10

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13282896Ethyl 2-amino-3-oxobutanoateHCID 86674514Tert-butoxycarbonylamino-5-benzyloxypentanoic acid dicyclohexylamine salt

Produkt 1

HCID 67395178ethyl 2-{[5-(benzyloxy)-N-(tert-butoxycarbonyl)-L-norvalyl]amino}-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

(S)-2-(tert-butoxycarbonylamino-5-benzyloxypentanoic acid dicyclohexylamine salt (10.0 g, 19.8 mmol) was purified by silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=19:1) in order to remove dicyclohexylamine. The resulting oil, ethyl 2-amino-3-oxobutanoate (3.60 g, 19.8 mmol), ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.69 g, 29.7 mmol), 1-hydroxybenzotriazole (4.01 g, 29.7 mmol), triethylamine (6.87 mL, 49.5 mmol), in chloroform (40 mL) was stirred for 6 h at room temperature, and then reaction mixture was poured into water. The organic layer was separated, washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2) to give ethyl 2-{[5-(benzyloxy)-N-(tert-butoxycarbonyl)-L-norvalyl]amino}-3-oxobutanoate. MS (APCI): m/z 468 (M+NH4).

Aufarbeitung

  1. customto remove dicyclohexylamine
  2. customreaction mixture
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-54f719a3939b487a968cd1add907863a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969376B2

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