Phosphoric Acid → (S)-N-((S)-5-((1-Ethyl-2-oxoindolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamide

HRID 1055463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1055463
P(=O)(O)(O)[OH:2].Cl[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:16][N:17]2[C:23](=[O:24])[C@@H:22]([NH:25][C:26](=[O:38])[C@@H:27]([N:29](C)[C:30](=O)OC(C)(C)C)[CH3:28])[CH2:21][O:20][C:19]3[CH:39]=[CH:40][CH:41]=[CH:42][C:18]2=3)[N:9]([CH2:43][CH3:44])[CH:8]=1>C([O-])(O)=O.[Na+]>[CH2:43]([N:9]1[C:10]2[C:15](=[C:14]([CH2:16][N:17]3[C:23](=[O:24])[C@@H:22]([NH:25][C:26](=[O:38])[C@@H:27]([NH:29][CH3:30])[CH3:28])[CH2:21][O:20][C:19]4[CH:39]=[CH:40][CH:41]=[CH:42][C:18]3=4)[CH:13]=[CH:12][CH:11]=2)[CH2:7][C:8]1=[O:2])[CH3:44]

Komponenten

4

Edukt 2

HCID 1004Phosphoric AcidHCID 131736364tert-butyl (S)-1-((S)-5-((3-chloro-1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Produkt 1

HCID 73055432(S)-N-((S)-5-((1-Ethyl-2-oxoindolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamideAusbeute 14,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Phosphoric acid (13.2 mg, 2 mL, 108 μmol, Eq: 1.00) was added to tert-butyl (S)-1-((S)-5-((3-chloro-1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (60 mg, 108 μmol, Eq: 1.00) and the mixture stirred at RT for 2 h. The mixture was diluted with sat. NaHCO3 and extracted with DCM. The combined extracts were concentrated and the residue was purified by preparative TLC to give the title compound (7 mg, 14%) as a solid. MS m/z 437 (MH+)

Aufarbeitung

  1. extractionextracted with DCM
  2. concentrationThe combined extracts were concentrated
  3. customthe residue was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-a13f11537ddb45eab2030ebe71f9a716
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394263B2

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