Triethylamine → 2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(5-methyl-hexanoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436513
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:38][CH:39]([CH3:46])[CH2:40][CH2:41][CH2:42][C:43](O)=[O:44].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:43](=[O:44])[CH2:42][CH2:41][CH2:40][CH:39]([CH3:46])[CH3:38])[CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 123445-Methylhexanoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 866153742-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866153782-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(5-methyl-hexanoyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dissolve (2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester (110 mg, 0.22 mmol) in 2.2 ml of dichloromethane and react with 5-methylhexanoic acid (28.6 mg, 0.22 mmol), EDCI (50.6 mg, 0.26 mmol), HOBT (35.6 mg, 0.26 mmol), triethylamine (0.09 ml, 0.66 mmol) and dimethylaminopyridine (2.6 mg, 0.02 mmol). Stir at room temperature overnight. Dilute with CH2Cl2, and wash with 5%NaHCO3 and saturated aqueous sodium chloride. Dry organic layers with MgSO4 and remove the solvent under reduced pressure. Subject residue to silica gel chromatography, eluting with hexanes/ethyl acetate/triethylamine 67:32:1 to obtain 103 mg (76% yield) of the desired product.

Aufarbeitung

  1. washwash with 5%NaHCO3 and saturated aqueous sodium chloride
  2. customDry organic layers with MgSO4 and remove the solvent under reduced pressure
  3. washSubject residue to silica gel chromatography, eluting with hexanes/ethyl acetate/triethylamine 67:32:1

Quellen und Nachweise

ORD-Eintrag
ord-d8e81a93d3c84310bf95b354b81a23c9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

Notizen zur Reaktion

Wird geladen…