Tetrahydrofuran → (3s)Tetrahydro-3-furanyl n-((1s,2r)-1-benzyl-3-sec-butoxy[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

HRID 1166491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166491
[NH2:1][C@@H:2]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:3]([OH:22])[CH2:4][N:5](OC(CC)C)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[O:30]1[CH2:34][CH2:33][C@H:32]([O:35][C:36]([O:38]N2C(=O)CCC2=O)=O)[CH2:31]1.[CH:46](N(C(C)C)CC)(C)C.[CH2:55]1C[O:58][CH2:57][CH2:56]1>>[CH2:23]([C@H:2]([NH:1][C:36](=[O:38])[O:35][C@H:32]1[CH2:33][CH2:34][O:30][CH2:31]1)[C@@H:3]([OH:22])[CH:4]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:7])=[O:8])[O:58][CH:57]([CH2:56][CH3:55])[CH3:46])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 11229944Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl EsterHCID 57264501N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(sec-butoxy)-4-methoxybenzene-sulfonamide

Produkt 1

HCID 69222762(3s)Tetrahydro-3-furanyl n-((1s,2r)-1-benzyl-3-sec-butoxy[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

Versuchsvorschrift

N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(sec-butoxy)-4-methoxybenzenesulfonamide (0.12 mmol, 50 mg), 1-([(3S)tetrahydro-3-furanyloxy]carbonyloxy)dihydro-1H-pyrrole-2,5-dione (0.12 mmol, 29 mg), diisopropylethylamine (0.18 mmol, 0.031 mL) and anhydrous THF (1 mL) were combined and stirred at room temperature for 20 hours. The reaction product was concentrated to a residue, purified directly by silica gel chromatography (2:1 hexanes/ethyl acetate) and crystallized from diethyl ether providing 40 mg (63%) of a white crystal. H1-NMR (CDCl3): δ7.74-7.70 (2H,m), 7.30-7.17 (6H,m), 7.00-6.96 (2H,m), 5.11 (1H,bs), 4.75 (1H,bs), 4.31-4.30 (1H,m), 3.87 (3H,s), 3.87-3.75 (6H,m), 3.65-3.60 (1H,m), 3.21-2.64 (1H,bs), 2.89 (2H,bs), 2.15-2.01 (1H,m), 1.95-1.78 (1H,m), 1.78-1.58 (1H,m), 1.47-1.32 (1H,m), 1.24-1.13 (3H,m), 0.94-0.84 (3H,m); MS (ESI): M+Na=560.

Aufarbeitung

  1. concentrationThe reaction product was concentrated to a residue
  2. custompurified directly by silica gel chromatography (2:1 hexanes/ethyl acetate)
  3. customcrystallized from diethyl ether providing 40 mg (63%) of a white crystal

Quellen und Nachweise

ORD-Eintrag
ord-e5adf598a5bb4f678d6bd4acd65e4ec7
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613743B2

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