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Water → (3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3-methylbutan-2-yl)-3-methylpiperidin-2-one

HRID 1048526
ノート
印刷プレビュー

反応式

HRID 1048526 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)O)[CH2:9][C@:10]([CH3:23])([CH2:20][CH:21]=[CH2:22])[C:11]([NH:13][C@@H:14]([CH:17]([CH3:19])[CH3:18])[CH2:15][OH:16])=[O:12])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.O>C1C=CC=CC=1.C(OCC)(=O)C.O1CCOCC1>[CH2:20]([C@@:10]1([CH3:23])[CH2:9][C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C@@H:24]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[N:13]([C@@H:14]([CH:17]([CH3:18])[CH3:19])[CH2:15][OH:16])[C:11]1=[O:12])[CH:21]=[CH2:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 88675Proton spongeHCID 67999646(S)-2-((2R,3R)-2-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N-((S)-1-hydroxy-3-methylbutan-2-yl)-2-methylpent-4-enamide

生成物 1

HCID 58573527
(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3-methylbutan-2-yl)-3-methylpiperidin-2-one

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

(S)-2-((2R,3R)-2-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-hydroxypropyl)-N—((S)-1-hydroxy-3-methylbutan-2-yl)-2-methylpent-4-enamide (example 261, step G) was transferred as a solution in anhydrous benzene to a pre-weighed, oven-dried 50 mL round bottom flask and stripped to dryness. Azeotropic distillation of benzene/water was performed twice more, and the residue was dried under high vacuum for 2 h, after which it weighed 550 mg. An oven-dried stir bar was added to the flask. The vessel was sealed and purged with nitrogen and then anhydrous dichloromethane (23 mL) was added, followed by triethylamine (1.3 mL, 9.33 mmol). The resulting stirred solution was cooled to 0° C. Methanesulfonyl chloride (0.270 mL, 3.49 mmol) was added dropwise by microsyringe. After 1 h, the reaction was quenched by addition of HCl (1.2M, 12 mL) and diluted in ethyl acetate. The organic layer was washed with 1.2 M HCl (30 mL), saturated sodium bicarbonate (2×25 mL), and sat. aq. NaCl solution. After drying over magnesium sulfate and concentration in vacuo an intermediate was obtained as an off-white foam (0.64 g,). 1,8-Bis(dimethylamino)naphthalene, 314 mg, 1.465 mmol) and water (0.104 mL, 5.75 mmol) were added to the intermediate, followed by dioxane (23 mL). The mixture was heated under nitrogen at 110° C. overnight. After cooling, the mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution.

後処理

  1. customoven-dried 50 mL round bottom flask
  2. distillationAzeotropic distillation of benzene/water
  3. customthe residue was dried under high vacuum for 2 h
  4. additionwas added to the flask
  5. customThe vessel was sealed
  6. custompurged with nitrogen
  7. additionanhydrous dichloromethane (23 mL) was added
  8. stirringThe resulting stirred solution
  9. customthe reaction was quenched by addition of HCl (1.2M, 12 mL)
  10. additiondiluted in ethyl acetate
  11. washThe organic layer was washed with 1.2 M HCl (30 mL), saturated sodium bicarbonate (2×25 mL), and sat. aq. NaCl solution
  12. dry with materialAfter drying over magnesium sulfate and concentration in vacuo an intermediate
  13. customwas obtained as an off-white foam (0.64 g,)
  14. temperatureThe mixture was heated under nitrogen at 110° C. overnight
  15. temperatureAfter cooling
  16. washwashed with saturated ammonium chloride solution

出典と根拠

ORDレコード
ord-fd1082f49f964a488036886182d6ef10
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569341B2

反応ノート

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