Benzoic Acid → (2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl Benzoate

HRID 1664259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664259
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.O[C@@H:32]1[CH2:37][C@@H:36]([CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[O:35][C@:34]([C@@H:45]2[CH2:49][S:48][C:47](=[O:50])[N:46]2[CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=2)([O:43][CH3:44])[CH2:33]1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.CCOCC>[C:1]([O:9][C@@H:32]1[CH2:37][C@@H:36]([CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[O:35][C@@:34]([O:43][CH3:44])([C@@H:45]2[CH2:49][S:48][C:47](=[O:50])[N:46]2[CH2:51][C:52]2[CH:53]=[CH:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=2)[CH2:33]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 59644055(R)-4-((2R,4R,6R)-4-Hydroxy-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

Produkt 1

HCID 59644040(2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl BenzoateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of benzoic acid (31.7 mg, 0.260 mmol) in dry toluene (5 mL) under a nitrogen atmosphere was added diisopropylethylamine (0.0435 mL, 0.250 mmol) and 2,4,6-trichlorobenzoyl chloride (0.0391 mL, 0.250 mmol). The mixture was stirred at room temperature for 3 h, after which the title compound from Example 14 (21.5 mg, 0.051 mmol) and DMAP (32.9 mg, 0.269 mmol) were added. This mixture was stirred at room temperature for 18 h, after which it was diluted with ether and washed with satd aq NH4Cl and brine, and the organic phase was dried and evaporated. Chromatography of the residue on silica gel, eluting with an ethyl acetate/dichloromethane gradient, afforded the title compound (21.7 mg, 81%) as an oil.

Aufarbeitung

  1. stirringThis mixture was stirred at room temperature for 18 h
  2. washwashed with satd aq NH4Cl and brine
  3. customthe organic phase was dried
  4. customevaporated
  5. washChromatography of the residue on silica gel, eluting with an ethyl acetate/dichloromethane gradient

Quellen und Nachweise

ORD-Eintrag
ord-dc26d78598ba4024988be08ee7a07e98
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039465B2

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