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 2261430노트

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HRID 2261430 반응식
[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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e1c889aa2104bb0a99e2da53015ca44
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846964B2

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