HCID 10774139、化合物 → HCID 21927928、化合物

HRID 585544ノート

反応式

HRID 585544 の反応式
[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]

参加物

6

反応物 3

HCID 10774139HCID 10774139、化合物2 回HCID 21927861HCID 21927861、化合物HCID 53249630Magnesium carbonate hydroxide pentahydrate

生成物 1

HCID 21927928HCID 21927928、化合物

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9b9802d4568b4b198898f0775587486a
出典データセット
uspto-grants-2005_08
特許番号
US06933304B2

反応ノート

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