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

HRID 29182

Reaktionsgleichung

Reaktionsgleichung von HRID 29182
[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-methoxybenzenesulfon-amide (0.12 mmol, 50 mg), 1-([(35)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): δ 7.74-7.70 (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-30c21f42147e40b6b8ff8af4fc2409ba
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419967B2

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