Pyrrole-2-Carboxylic Acid → HCID 69817910, Verbindung

HRID 2417426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417426
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([N:12]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][C@H:14]([OH:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1.[NH:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:24]([N:12]([C@H:9]([CH2:10][OH:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:36]([C:32]2[NH:31][CH:35]=[CH:34][CH:33]=2)=[O:37])=[CH:3][CH:4]=1)[CH2:13][C@H:14]([OH:23])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 3

HCID 12473Pyrrole-2-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69817666HCID 69817666, Verbindung

Produkt 1

HCID 69817910HCID 69817910, VerbindungAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-1-propanol (79 mg) and pyrrole-2-carboxylic acid (26 mg) in dichloromethane (0.8 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (59 mg), and the mixture was stirred at room temperature for 47 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give N-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]-phenyl]-1H-pyrrole-2-carboxamide (48 mg) as a white amorphous powder.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e5fe96b9f6314ce397451bf9f8fc705e
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06826033B2

Notizen zur Reaktion

Wird geladen…