Ammonium Chloride → tert-butyl (5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oate

HRID 879234

Reaktionsgleichung

Reaktionsgleichung von HRID 879234
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]([CH3:26])[C@H:19]([C:23](O)=[O:24])[CH:20]([CH3:22])[CH3:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:27]([O:31][C:32](=[O:51])[CH2:33][C@@H:34]([O:49][CH3:50])[C@@H:35]([N:40]([CH3:48])[C:41](=[O:47])[C@H:42]([CH:44]([CH3:46])[CH3:45])[NH2:43])[C@@H:36]([CH3:39])[CH2:37][CH3:38])([CH3:30])([CH3:29])[CH3:28].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]([CH3:26])[C@H:19]([C:23]([NH:43][C@H:42]([C:41]([N:40]([C@@H:35]([C@@H:36]([CH3:39])[CH2:37][CH3:38])[C@H:34]([O:49][CH3:50])[CH2:33][C:32]([O:31][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:51])[CH3:48])=[O:47])[CH:44]([CH3:45])[CH3:46])=[O:24])[CH:20]([CH3:21])[CH3:22])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 978328(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methylbutanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10546343(3R,4S,5S)-tert-butyl 4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate2×

Produkt 1

HCID 71294595tert-butyl (5S,8S,11S,12R)-11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-2-oxa-4,7,10-triazatetradecan-14-oate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

396 mg (1.1 mmol) N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine were dissolved in 20 ml DMF and 365 mg (1 mmol) tert.-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoate (intermediate 2), 234 mg (1.2 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 187 mg (1.2 mmol) 1-hydroxy-1H-benzotriazol hydrate were added in succession. The mixture was stirred overnight at RT. 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 residue was used directly in the next step, without purification.

Aufarbeitung

  1. customThe organic phase was separated off
  2. washwashed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was used directly in the next step, without purification

Quellen und Nachweise

ORD-Eintrag
ord-7059a438341646f19614e2c794908029
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987209B2

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