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Propionic Acid → 5(S)-[1(S)-(Boc-Amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one

HRID 2394159
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2394159
[C:1]([NH:8][C@H:9]([C@H:22]1[O:26][C:25](=[O:27])[CH2:24][CH2:23]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:38]([O:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50]I)=[CH:48][CH:47]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O)(=O)CC>C1COCC1.CN1C(=O)N(C)CCC1.C(OCC)(=O)C.O>[C:1]([NH:8][C@H:9]([C@H:22]1[O:26][C:25](=[O:27])[C@H:24]([CH2:50][C:49]2[CH:52]=[CH:53][C:46]([O:45][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:47][CH:48]=2)[CH2:23]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 1032Propionic AcidHCID 2733832Lithium hexamethyldisilazaneHCID 11723738p-Benzyloxybenzyl iodideHCID 541918735(S)-[1(S)-(Boc-Amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]dihydrofuran-2-(3H)-one

Produkt 1

HCID 701494025(S)-[1(S)-(Boc-Amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittelHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under an N2 atmosphere, 3,6 g (9,48 mmol) of 5(S)-[1(S)-(Boc-amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]dihydrofuran-2-(3H)-one, dissolved in 17.3 ml of THF and 1.9 ml of DMPU, are deprotonated, at -70° C., with 18.58 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and, after 15 min, alkylated with 3.07 g (9.48 mmol) of p-benzyloxybenzyl iodide (Example 1d)) in 6 ml of THF. After 30 min at -75° C., the mixture is protonated with 3.53 ml (47.4 mmol) of propionic acid and 3.53 ml of water and warmed to 0° C. The reaction mixture is diluted with 95 ml of ethyl acetate and the whole is washed with 10% citric acid solution, sat. NaHCO3 solution and saline. The aqueous phases are extracted with 2 portions of ethyl acetate. The organic phases are dried with Na2SO4 and evaporated. Column chromatography (SiO2, hexane/ethyl acetate, 1:1) and crystallization from ethyl acetate/hexane yields the pure title compound: TLC Rf (C)=0.38; tRet (II)=18.0 min; FAB-MS (M+H)+ =576.

Aufarbeitung

  1. waitAfter 30 min at -75° C.
  2. washthe whole is washed with 10% citric acid solution, sat. NaHCO3 solution and saline
  3. extractionThe aqueous phases are extracted with 2 portions of ethyl acetate
  4. dry with materialThe organic phases are dried with Na2SO4
  5. customevaporated
  6. customColumn chromatography (SiO2, hexane/ethyl acetate, 1:1) and crystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6df1b63a1aa1468bb12d7d798766157c
Quelldatensatz
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05807891

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