(3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone → (3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(3R)-6-methoxycarbonyl-4-oxochroman-3-yl]-azetidin-2-one

HRID 1654003

Reaktionsgleichung

Reaktionsgleichung von HRID 1654003
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.[O:20]=[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=2)[O:24][CH2:23][CH2:22]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:13]([O:12][C@@H:10]([C@@H:6]1[C@@H:5]([C@H:22]2[C:21](=[O:20])[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=3)[O:24][CH2:23]2)[NH:8][C:7]1=[O:9])[CH3:11])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

Komponenten

4

Edukt 2

HCID 13073890(3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinoneHCID 23513066Methyl 4-oxochromane-6-carboxylate

Produkt 1

HCID 67788530(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(3R)-6-methoxycarbonyl-4-oxochroman-3-yl]-azetidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584019Toluene ethylacetateLösungsmittel

Versuchsvorschrift

Starting from 960 mg (3.35 mmol) of (3S, 4R)-4-acetoxy-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-azetidin-2-one and 1.03 g (5.0 mmol) of methyl 4-oxochroman-6-yl carboxylate, 370 mg (25%) of the less polar diastereomer were obtained after chromatography (eluent: toluene/ethyl acetate=10: 1, 1.11, then 2:1) as described under step 1 in Example 14. -1H-NMR (270 MHz, CDCl3): 6 m 0.08 and 0.10 (2×1s, 2×3H, SiCH3); 0.90 (s, 9H, SiC(CH3)3); 1.28 (d, 3H, CH--CH3); 2.85-2.98 (m, 2H, O--CH2 --CH and H-3); 3.72 (dd, 1H, H-4); 3.92 (s, 3H, CO2CH3); 4.18 (mc, 1H, CH--CH3); 4.32 and 4.65 (2×mc, 2×1H, O--CH2 --CH); 6.26 (bs, 1H, NH); 7.03 (d, 1H, aromatic H); 8.18 (dd, 1H, aromatic H) 8.59 (d, 1H, aromatic H).

Aufarbeitung

  1. customwere obtained after chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-4d5c99b83ee54e4f859da87b46854b26
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405844

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