Hydrochloric Acid → Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate

HRID 415176

Reaktionsgleichung

Reaktionsgleichung von HRID 415176
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[C:23](=[C:25]([C:29](O)=[O:30])[CH:26]=[CH:27][CH:28]=3)[N:24]=2)=[CH:16][CH:15]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=[N:38]C=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[Cl-].[NH4+].Cl>CN(C)C=O.O>[C:29]([C:25]1[C:23]2[N:24]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([CH2:13][N:11]([CH3:12])[C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:15][CH:16]=3)[O:21][C:22]=2[CH:28]=[CH:27][CH:26]=1)(=[O:30])[NH2:38]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 666205582-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid

Produkt 1

HCID 66621310Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamateAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid, (0.060 g, 0.14 mmol) in dimethyl formamide (10 mL) was added HOBT (0.025 g, 0.165 mmol), EDCI (0.035 g, 0.18 mmol), DIPEA (0.058 g, 0.45 mmol) and ammonium chloride (0.008 g, 0.15 mmol). The reaction mixture was stirred at room temperature for 20 hr, cooled and poured into water (10 mL). The pH was adjusted to 3 with 1N aqueous hydrochloric acid. The solution was extracted with dichloromethane (70 mL×3). The solution was washed with brine, dried, condensed in vacuum and separated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1) to afford benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate 0.045 g solid (yield: 75.2%); LC-MS (ESI) m/z 416 [M+1]+.

Aufarbeitung

  1. temperaturecooled
  2. extractionThe solution was extracted with dichloromethane (70 mL×3)
  3. washThe solution was washed with brine
  4. customdried
  5. customcondensed in vacuum
  6. customseparated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e7c06e315af64afd9ad7aa288d3e2afa
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

Verknüpfte Notizen

Wird geladen…