Ammonia → Benzyl 2-{[2-amino-3-(aminocarbonyl)phenyl]amino}-1,1-dimethyl-2-oxoethylcarbamate

HRID 1512702

Reaktionsgleichung

Reaktionsgleichung von HRID 1512702
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:32][C:33]1[C:41]([NH2:42])=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([NH2:37])=[O:36].N>N1C=CC=CC=1.CN(C=O)C>[NH2:32][C:33]1[C:34]([C:35]([NH2:37])=[O:36])=[CH:38][CH:39]=[CH:40][C:41]=1[NH:42][C:13](=[O:15])[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 534228072,3-Diaminobenzamide dihydrochloride

Produkt 1

HCID 68512848Benzyl 2-{[2-amino-3-(aminocarbonyl)phenyl]amino}-1,1-dimethyl-2-oxoethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

2-{[(Benzyloxy)carbonyl]amino}-2-methylpropanoic acid (5.18 g, 21.83 mmol) in a mixture of pyridine (25 mL) and DMF (25 mL) was treated with 1,1′-carbonyldiimidazole (3.72 g, 22.92 mmol) and heated at 40° C. for 2 hours. 2,3-Diaminobenzamide dihydrochloride (4.89 g, 21.83 mmol), prepared as described in WO0026192, was added and the mixture was stirred at room temperature overnight. The solvents were removed under vacuum and the residue was partitioned between ethyl acetate and diluted sodium bicarbonate aqueous solution. The formed slightly yellow solid material was collected by filtration, washed with water and ethyl acetate, and dried to give Example 1A. MS (DCI/NH3) m/z 371 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. customThe solvents were removed under vacuum
  3. customthe residue was partitioned between ethyl acetate and diluted sodium bicarbonate aqueous solution
  4. customThe formed slightly yellow solid material
  5. filtrationwas collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried
  8. customto give Example 1A

Quellen und Nachweise

ORD-Eintrag
ord-f3f3a3a79c3241adb0da397c6bef082a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217070B2

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