HCID 10774139, 화합물 → HCID 21927928, 화합물

HRID 1243507노트

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HRID 1243507 반응식
[NH2:1][C:2](=[S:12])[CH2:3][C:4]([CH3:11])([CH3:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].O.O.O.O.O.[OH-].C(=O)(O)[O-].[Mg+2].[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=O)[CH2:33]Cl)(=[O:26])[CH3:25]>O1CCOCC1.C(OCC)(=O)C>[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[N:1]=[C:2]([CH2:3][C:4]([CH3:10])([CH3:11])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[S:12][CH:33]=1)(=[O:26])[CH3:25]

참가 물질

6

반응물 3

HCID 10774139HCID 10774139, 화합물2회HCID 21927861HCID 21927861, 화합물HCID 53249630Magnesium carbonate hydroxide pentahydrate

생성물 1

HCID 21927928HCID 21927928, 화합물

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

Methyl 5-amino-3,3-dimethyl-5-thioxopentanoate (500 mg; 2.64 mmoles) was dissolved in 1,4-dioxane (10 mL) under nitrogen and magnesium carbonate hydroxide pentahydrate (640 mg; 1.32 mmoles) was added. 6-Chloro-5-oxohexyl acetate (685 mg; 3.56 mmoles; Rieke, R. D.; Brown, J. D.; Wu, X. Synth. Commun. 1995, 25(23), 3923.) was added and the mixture was magnetically stirred for 10 hours with heating to 60° C. The mixture was allowed to cool, diluted with ethyl acetate and filtered. The solvent was removed under vacuum and the residue was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (3:1). Following removal of solvent the product, methyl 4-{4-[4-(acetyloxy)butyl]-1,3-thiazol-2-yl}-3,3-dimethylbutanoate, was obtained as pale yellow oil. (820 mg). The material was impure, containing some 6-Chloro-5-oxohexyl acetate. 1H NMR (400 MHz) CDCl3 δ 6.76 (1H, s), 4.04–4.11 (2H, m), 3.68 (3H, m), 3.05 (2H, s), 2.78 (2H, t, J=7.5 Hz), 2.33 (2H, s), 2.04 (3H, s), 1.61–1.82 (4H, m), 1.10 (6H, s).

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel
  5. washeluting with hexane/ethyl acetate (3:1)
  6. customremoval of solvent the product, methyl 4-{4-[4-(acetyloxy)butyl]-1,3-thiazol-2-yl}-3,3-dimethylbutanoate
  7. customwas obtained as pale yellow oil

출처 및 근거

ORD 기록
ord-b250397f8a614167b4f7154b269845bc
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119098B2

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