4-Methylmorpholine → HCID 68157449, Verbindung

HRID 242778

Reaktionsgleichung

Reaktionsgleichung von HRID 242778
[C:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O:19][C:20]([NH:22][CH:23]([CH3:27])[C:24](O)=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[C:15]([O:19][C:20](=[O:21])[NH:22][CH:23]([C:24](=[O:25])[NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:27])([CH3:16])([CH3:17])[CH3:18]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 68297N-Phenyl-o-phenylenediamineHCID 757711-HydroxybenzotriazoleHCID 2684712-N-Boc-aminopropionic acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×

Produkt 1

HCID 68157449HCID 68157449, VerbindungAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Phenylbenzene-1,2-diamine (1.84 g, 0.01 mol), racemic (R/S)-2-tertbutoxycarbonylaminopropionic acid (1.89 g, 0.01 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.92 g), 4-methylmorpholine (1.0 g, 0.01 mol), HOBt (1.53 g, 0.01 mol) were suspended in THF (10 mL) under a nitrogen atmosphere. The resulting mixture was stirred for 12 h at RT. After this period of time, additional amounts of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (500 mg×3) and of (R/S)-2-tertbutoxycarbonylaminopropionic acid (500 mg) were added and the mixture was stirred for further 4 h. The reaction mixture was then partitioned between water and EtOAc. The organic layer was separated, dried (MgSO4) and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC ISCO 24 g column, gradient 0-20% EtOAc in cyclohexane). The product containing fractions were combined and concentrated in vacuo affording [1-(2-Phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester as a white crystalline solid (3.07 g, 86%). LCMS: RT 3.61 min [M+H-tBu]+ 300.1.

Aufarbeitung

  1. stirringthe mixture was stirred for further 4 h
  2. customThe reaction mixture was then partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified by column chromatography (Si—PCC ISCO 24 g column, gradient 0-20% EtOAc in cyclohexane)
  7. additionThe product containing fractions
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-be45b9672691469baf49983c9874d67e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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