Triethylamine → t-Butyl 2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(RS)-tetrahydropyran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate

HRID 1421788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421788
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[C@@H:14]([S:15][CH2:16][C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)=[O:18])[NH:13][C:12]2=[O:25])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])[CH:27]=[O:28].C(N(CC)CC)C.C(OCC)(=O)C>ClCCCl>[OH:28][CH:27]([N:13]1[C@H:14]([S:15][CH2:16][C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[O:18])[C@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:25])[C:26]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10986247Tert-butyl 2-oxoacetateHCID 18396289(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydropyran-2-yl-carbonylmethylthio]azetidin-2-one

Produkt 1

HCID 18397160t-Butyl 2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(RS)-tetrahydropyran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydropyran-2-yl-carbonylmethylthio]azetidin-2-one (1.7 g) in 1,2-dichloroethane (20 ml) was successively treated with 0.5M t-butyl glyoxylate in 1,2-dichlorethane (10 ml) and triethylamine (50 mg, 70 μl) and monitored by t.l.c. (ethyl acetate) until no starting material remained. The reaction mixture was concentrated and flash chromatography (70% ethyl acetate in hexane, ethyl acetate) to afford the title compound as a yellow foam (1.9 g, 82%); νmax (CH2Cl3) 3400 (w), 1780, 1736, 1687 cm-1 ; δH (CDCl3) 1.49 (9H, s) overlapping 1.44-1.61 (4H, m), 1.8-2.0 (2H, m), 3.35-3.58 (3H, m), 3.65 (2H, s), 3.81-3.92 (1H, m), 4.01-4.06 (1H, m), 4.28-4.43 (1H, m), 4.99, 5.00, 5.07 (together 1H, 3d, J4.7 Hz), 5.21, 5.32, 5.33 (together 1H, 3d, J6.8, 7.7, 7.6 Hz), 5.42, 5.50 (together 1H, 2dd, J4.8, 8.7 Hz, 6.35, 6.36, 6.61 (together 1H, 3d, J8.7 Hz) and 7.27-7.38 (5H, m).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3519d2157cec4acd902cf4f6a800a75c
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077952

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