Tris(hydroxymethyl)aminomethane → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenylbenzamide

HRID 1612479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612479
N=C=N.C1C=CC2N(O)N=NC=2C=1.[O:14]=[C:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]1[CH:21]=[C:22]([C:32](O)=[O:33])[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1.[CH3:35][C:36]([CH3:57])([CH3:56])[CH2:37][CH2:38][NH:39][C:40](=[O:55])[C@H:41]([CH3:54])[CH2:42][C@H:43]([OH:53])[C@@H:44]([NH2:52])[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(O)C(N)(CO)CO.[N-]=C=O>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[CH2:45]([C@H:44]([NH:52][C:32](=[O:33])[C:22]1[CH:23]=[C:24]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:25]=[C:20]([N:16]2[CH2:17][CH2:18][CH2:19][C:15]2=[O:14])[CH:21]=1)[C@@H:43]([OH:53])[CH2:42][C@H:41]([C:40](=[O:55])[NH:39][CH2:38][CH2:37][C:36]([CH3:56])([CH3:35])[CH3:57])[CH3:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Komponenten

9

Edukt 6

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435CarbodiimideHCID 222529945-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic AcidHCID 68890142(2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide

Produkt 1

HCID 10129098N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel2×

Versuchsvorschrift

Polystyrene linked carbodiimide (21 mg, 1.7 mmol/g, 0.036 mmol) was placed in a vial with DCM (1 ml). To this was added HOBT (5 mg, 0.036 mmol) in 1 ml DCM/DMF=4:1, 5-(2-oxo-pyrrolidin-1-yl)-biphenyl-3-carboxylic acid (D11) (10 mg, 0.036 mmol) in 1 ml DCM/DMF=4:1, and (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)amide (D2) (in 1 ml DCM). The mixture was stirred at room temperature overnight. Scavenger resins trisamine (˜100 mg) and isocyanate (˜100 mg) were added and the mixture was stirred for another 1.5 hours. The resins were filtered and the solvent evaporated in vacuo. Column chromatography on silica gel (5% MeOH in DCM) gave E6 (5 mg).

Aufarbeitung

  1. stirringthe mixture was stirred for another 1.5 hours
  2. filtrationThe resins were filtered
  3. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-57cf193524084a2cb1c08697fd036056
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992103B2

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