Sodium cyanoborohydride → HCID 86727465, Verbindung

HRID 519093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519093
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=O)[CH:9]1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:16]=[C:17]2[C:26](=[CH:27][CH:28]=1)[O:25][CH2:24][C:23]1[N:18]2[CH:19]([CH3:30])[C:20](=[O:29])[NH:21][N:22]=1.[BH3-]C#N.[Na+]>CO.CC(O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:14][C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][CH:28]=2)[O:25][CH2:24][C:23]2[N:18]3[CH:19]([CH3:30])[C:20](=[O:29])[NH:21][N:22]=2)[CH:9]1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 722080901-Azetidinecarboxylic acid, 2-methyl-3-oxo-, 1,1-dimethylethyl esterHCID 867272916-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

Produkt 1

HCID 86727465HCID 86727465, VerbindungAusbeute 18,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 2-methyl-3-oxo-azetidine-1-carboxylic acid tert-butyl ester (crude, 1.17 mmol) in MeOH (5 mL) and AcOH (0.5 mL) was added 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #2, Step E, 0.050 g, 0.215 mmol). The reaction mixture was stirred at ambient temperature for 0.5 h then NaBH3CN (0.068 g, 1.076 mmol) was added. The mixture was stirred at ambient temperature overnight then concentrated in vacuo. The residue was purified by preparative HPLC (Table 3, Method 24) to give 2-methyl-3-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.016 g, 18%). LC/MS (Table 1, Method 5) Rt=1.087 min; MS m/z: 424 [M+23]+.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by preparative HPLC (Table 3, Method 24)

Quellen und Nachweise

ORD-Eintrag
ord-1caf26f4d96043e0a393d9e369bc6830
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115151B2

Notizen zur Reaktion

Wird geladen…