Hexane → N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester

HRID 23885

Reaktionsgleichung

Reaktionsgleichung von HRID 23885
[CH:1]1([C:10]([NH:12][C@H:13]([C:32]([O:34][CH3:35])=[O:33])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[C:28]([Cl:29])=[CH:27][N:26]=[CH:25][C:24]=3[Cl:30])=[CH:17][CH:16]=2)=[O:11])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][NH:2]1.[C:36]1([CH3:46])[CH:41]=[CH:40][CH:39]=[C:38]([S:42](Cl)(=[O:44])=[O:43])[CH:37]=1.CCN(C(C)C)C(C)C.CCCCCC>C(Cl)Cl.C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:46][C:36]1[CH:37]=[C:38]([S:42]([N:2]2[CH2:3][CH:4]3[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:1]2[C:10]([NH:12][C@H:13]([C:32]([O:34][CH3:35])=[O:33])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[C:28]([Cl:29])=[CH:27][N:26]=[CH:25][C:24]=3[Cl:30])=[CH:17][CH:16]=2)=[O:11])(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1

Komponenten

9

Edukt 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 27345953-Methylbenzenesulphonyl chlorideHCID 131724739HCID 131724739, Verbindung

Produkt 1

HCID 131724738N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl esterAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(Octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester (30 mg) was dissolved in 0.15 each of CH2Cl2 and THF. To this was added m-toluenesulfonyl chloride (0.051 mmol, 9.7 mg), followed by DIPEA (0.153 mmol, 20 mg) and 4-DMAP (0.01 mmol, 1.24 mg). This mixture was stirred at rt overnight when TLC (1:2 hexane:ethyl acetate) indicated the disappearance of all starting material. The volatiles were removed in vacuo and the residue was purified by flash column chromatography on silica gel eluted with a gradient of hexane and EtOAc to yield N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester (35 mg) as a sticky foam (homogeneous by TLC (1:2 hexane:ethyl acetate)).

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel
  3. washeluted with a gradient of hexane and EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-a59eaf0caec044798153e237ff72f9c6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855708B2

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