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Benzylamine → (S)-N-Benzyl-2-(Boc-amino)-2-phenylacetamide

HRID 489991
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 489991
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid

Produkt 1

HCID 12148799(S)-N-Benzyl-2-(Boc-amino)-2-phenylacetamideAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

(S)-tert-Butoxycarbonylamino-phenyl-acetic acid (1.00 g, 4 mmol) was dissolved in DCM (15 mL). Benzylamine (0.428 g, 4 mmol) and DIEA(0.65 g, 5 mmol) were added to the above mixture. The mixture which resulted was stirred at room temperature for a few minutes. PyBroP(2.10 g, 4.5 mmol) was added to the above solution in one portion and the reaction mixture was stirred overnight. The reaction mixture was diluted with DCM (150 mL) and washed with NaHCO3 (50 mL×2, sat.). The organic layer was collected and dried (Na2SO4) and the solvent was removed under reduced pressure. The crude product was purified by chromatography to provide the desired product (0.85 g, 62%).

Aufarbeitung

  1. customThe mixture which resulted
  2. stirringthe reaction mixture was stirred overnight
  3. washwashed with NaHCO3 (50 mL×2, sat.)
  4. customThe organic layer was collected
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2468173820694f898002cd4a22233aac
Quelldatensatz
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06979692B2

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