Hydrochloric Acid → (5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acid

HRID 1755817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755817
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([O:24]C)=[O:23])[C:17](=[O:26])[CH:16]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([OH:24])=[O:23])[C:17](=[O:26])[CH:16]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86748875methyl (5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoate

Produkt 1

HCID 54027587(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of the above ester (35) (1.2 g) in dioxane (12 mL) was added a solution of NaOH (5.3 mL, 1N in H2O). After stirring for 4 h at room temperature 1N HCl (5.3 mL) was added and the reaction extracted with ethyl acetate, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (37) was obtained by flash chromatography (silica gel, 98:2:0.1 CHCl3 :MeOH:HOAc) (1.0 g, 86%). TLC Rf 0.53 (95:4:1 CHCl3 :MeOH:HOAc); MS DC I/NH3 (M+H)+ =436.3; 1H NMR (CDCl3) δ1.13(3H, d, J=7 Hz ), 1.6-3.3 (9H, m), 3.65 (1H, m), 4.1 (1H, br m), 5.1 (2H, s), 5.45(1H, d), 7.2(5H, s), 7.35(5H, s), 10.65 (1H, br s).

Aufarbeitung

  1. additionwas added
  2. extractionthe reaction extracted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a1a359c522584514871aa836d8ce3a96
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05438118

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