Ammonium formate → HCID 71465770, Verbindung

HRID 2201691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201691
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:26])[O:17][CH2:18][CH:19]1[CH2:22][N:21]([C:23](=[O:25])[CH3:24])[CH2:20]1)([O-])=O.C([O-])=O.[NH4+]>CO.C1COCC1.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:26])[O:17][CH2:18][CH:19]1[CH2:22][N:21]([C:23](=[O:25])[CH3:24])[CH2:20]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 71007323(1-Acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

Produkt 1

HCID 71465770HCID 71465770, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (1-acetylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.15 g, 0.40 mmol, 1 eq.) in MeOH/THF (5 mL/5 mL) was added Zinc powder (0.13 g, 2.00 mmol, 5 eq.) and ammonium formate (0.20 g, 3.20 mmol, 8 eq.). The reaction was stirred at room temperature for 3 h. The reaction was filtered through Celite and the solids washed with MeOH. The filtrate was concentrated under reduced pressure then diluted with water. The obtained solid was filtered and dried. The crude product was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2) to obtain (1-acetylazetidin-3-yl)methyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate (0.030 g, 22% yield). ESI+ MS: m/z 346 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 8.74 (bs, 1H), 7.50 (bs, 1H), 7.34 (d, J=5.0 Hz, 1H), 7.24-7.14 (m, 2H), 7.08-7.01 (m, 1H), 6.72 (d, J=8.0 Hz, 1H), 5.14 (bs, 2H), 4.30-4.10 (m, 3H), 3.95-3.80 (m, 2H), 3.68-3.55 (m, 1H), 2.95-2.85 (m 1H), 1.74 (s, 3H).

Aufarbeitung

  1. filtrationThe reaction was filtered through Celite
  2. washthe solids washed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionthen diluted with water
  5. filtrationThe obtained solid was filtered
  6. customdried
  7. customThe crude product was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-a98d7b797a9140fa94299c46fe0e3b5d
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365498B2

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