4-Methylmorpholine → HCID 69861742, Verbindung

HRID 323709

Reaktionsgleichung

Reaktionsgleichung von HRID 323709
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.CN1CCOCC1.[NH2:21][C@@H:22]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:23][OH:24].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)C.CO>[OH:24][CH2:23][C@@H:22]([NH:21][C:11]([C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:13])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

9

Edukt 5

HCID 79724-MethylmorpholineHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 447213phenylalaninol, (S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 69861742HCID 69861742, VerbindungAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1-methyl-2-indolecarboxylic acid (100 mg, 0.57 mmol) in methylene chloride (1 mL) was added N-methylmorpholine (0.063 mL, 0.57 mmol) followed by (S)-(−)-2-amino-3-phenyl-1-propanol (86 mg, 0.57 mmol), 1-hydroxybenzotriazole hydrate (81 mg, 0.60 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (120 mg, 0.63 mmol). The resulting mixture was stirred at room temperature for 20 h. The reaction was diluted with methylene chloride and washed sequentially with 10% citric acid, saturated NaHCO3, water, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude oil. Trituration of the crude oil with methanol and diethyl ether afforded the title compound (68%, 119.7 mg) as an off-white solid. MS (ES) m/e 309.4 [M+H]+.

Aufarbeitung

  1. washwashed sequentially with 10% citric acid, saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give a crude oil

Quellen und Nachweise

ORD-Eintrag
ord-ba43aa1208ed46849711ebd9f4436e12
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214856B1

Verknüpfte Notizen

Wird geladen…