Hydrochloric Acid → 3-(3,5-diethyl-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one

HRID 2261430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261430
[CH3:1][C:2]1([CH3:15])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12](=[O:14])[CH3:13].[CH2:16]([C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([CH2:27][CH3:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:17].COC([C@@H](NC([C@@H](N)CC(O)=O)=O)CC1C=CC=CC=1)=O.Cl.Cl>C(O)C.C(O)(C)C.CC(=O)OCC>[CH2:16]([C:18]1[CH:19]=[C:20]([CH2:21][CH2:13][C:12]([C:7]2[S:8][C:9]([CH3:11])=[C:10]3[C:6]=2[CH2:5][C@H:4]2[C:2]([CH3:15])([CH3:1])[C@H:3]23)=[O:14])[CH:23]=[C:24]([CH2:27][CH3:28])[C:25]=1[OH:26])[CH3:17]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 134600L-Phenylalanine, L-alpha-aspartyl-, 2-methyl ester, hydrochloride (1:1)HCID 30179473,5-Diethyl-4-hydroxybenzaldehydeHCID 59380608(1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone

Produkt 1

HCID 595935433-(3,5-diethyl-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pen-talen-4-yl)-ethanone (890 mg, 4.04 mmol) and 3,5-diethyl-4-hydroxy-benzaldehyde (900 mg, 5.05 mmol, Lit: G. Trapani, A. Latrofa, M. Franco, C. Altomare, E. Sanna, M. Usal, G. Biggio, G. Liso J. Med. Chem. 41 (1998) 1846-1854; G. G. Ecke, J. P. Napolitano, A. H. Bilbey, A. J. Kolka, J. Org. Chem. 22 (1957) 639-642) in ethanol (7.5 mL) and 5 N HCl in isopropanol (2.5 mL) is stirred at rt for 72 h. The mixture is diluted with EA and is washed with water. The sovent of the organic layer is evaporated, the residue is dissolved in ethanol, treated with Pd/C (200 mg, 10% Pd) and stirred at rt for 18 h under 1.8 bar H2. The mixture is filtered, the filtrate is concentrated and the crude product is purified by CC on silica gel eluting with heptane:EA 8:2 to give 3-(3,5-diethyl-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (1.05 g) as a yellow oil; LC-MS: tR=1.15 min, [M+1]+=383.25.

Aufarbeitung

  1. washis washed with water
  2. customThe sovent of the organic layer is evaporated
  3. dissolutionthe residue is dissolved in ethanol
  4. additiontreated with Pd/C (200 mg, 10% Pd)
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated
  7. customthe crude product is purified by CC on silica gel eluting with heptane:EA 8:2

Quellen und Nachweise

ORD-Eintrag
ord-0e1c889aa2104bb0a99e2da53015ca44
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846964B2

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