Potassium Carbonate → 4-Methoxybenzyl (6R,7R)-7-Amino-3-((R)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

HRID 1421806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421806
O[CH:2]([N:15]1[C:21](=[O:22])[C@@H:20]2[C@H:16]1[S:17][C:18]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=CC=1)=[N:19]2)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].O.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.BrCC([C@H]1CCCO1)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CC(C)=O.O>[NH2:19][C@@H:20]1[C:21](=[O:22])[N:15]2[C:2]([C:3]([O:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)=[O:4])=[C:23]([C@H:24]3[CH2:29][CH2:28][CH2:27][O:38]3)[CH2:18][S:17][C@H:16]12

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 111948672-Bromo-1-[(2R)-tetrahydro-2-furanyl]-ethanoneHCID 536561234-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate

Produkt 1

HCID 538410274-Methoxybenzyl (6R,7R)-7-Amino-3-((R)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Methoxybenzyl (RS)-2-hydroxy-2-[(1R,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-on-6-yl]acetate (4.103 g) in dichloromethane (15 ml) and acetone (15 ml) was ring opened with 4-toluenesulphonic acid hydrate (3.33 g) in water (8 ml) and coupled to (R)-2-bromoacetyltetrahydrofuran (2.11 g) in acetone (20 ml) with potassium carbonate (0.687 g) as described in Example 6(b) for the diastereoisomeric mixture. After purification by flash chromatography, the title compound was obtained as a yellow gum (2.618 g, 49%); [α]D -10.7 (c 1.00 CHCl3).

Aufarbeitung

  1. customAfter purification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d6a17ee4d5846b4bcc4dd611a5f0efd
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077952

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