Ammonium Chloride → (3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

HRID 879232

Reaktionsgleichung

Reaktionsgleichung von HRID 879232
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:20]([O:24][C:25](=[O:37])[CH2:26][C@@H:27]([O:35][CH3:36])[C@@H:28]([NH:33][CH3:34])[C@@H:29]([CH3:32])[CH2:30][CH3:31])([CH3:23])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:20]([O:24][C:25](=[O:37])[CH2:26][C@@H:27]([O:35][CH3:36])[C@@H:28]([N:33]([C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:34])[C@@H:29]([CH3:32])[CH2:30][CH3:31])([CH3:22])([CH3:21])[CH3:23]

Komponenten

9

Edukt 6

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 726987N-Carbobenzoxy-L-valine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27960291-Hydroxybenzotriazole hydrate2×HCID 14730240(3r,4s,5s)-Tert-butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride2×

Produkt 1

HCID 10529182(3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

425 mg (1.7 mmol) N-[(benzyloxy)carbonyl]-L-valine were dissolved in 50 ml of DMF and mixed successively with 500 mg (1.7 mmol) of tert.-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)-heptanoate hydrochloride (starting compound 2), 356 mg (1.9 mmol) 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 285 mg (1.9 mmol) 1-hydroxy-1H-benzotriazol hydrate and 655 mg (5.1 mmol) of N,N-iiisopropylethylamine. The mixture was stirred for 20 h at RT. Another 142 mg (0.5 mmol) of N-[(benzyloxy)carbonyl]-L-valine, 119 mg (0.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 95 mg (0.6 mmol) of 1-hydroxy-1H-benzotriazol hydrate and 218 mg (1.7 mmol) N,N-diisopropylethylamine were added and the mixture was treated with ultrasound for 90 min. The mixture was then poured into a solution of semi-saturated aqueous ammonium chloride and ethyl acetate. The organic phase was separated off, washed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, then dried over magnesium sulphate, filtered and evaporated. The remainder was purified using preparative HPLC. 329 mg (40% o. th.) of the title compound were obtained as a colorless oil.

Aufarbeitung

  1. additionthe mixture was treated with ultrasound for 90 min
  2. customThe organic phase was separated off
  3. washwashed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe remainder was purified

Quellen und Nachweise

ORD-Eintrag
ord-7aa6229f673f4f46bad25b640104f9e8
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987209B2

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