5-Methyl-2-(tri-n-butylstannyl)pyridine → tert-butyl (4S,5S)-4-benzyl-5-{2-{[(benzyloxy)carbonyl]amino}-3-[4-(5-methyl-2-pyridinyl)phenyl]propyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1174333ノート

反応式

HRID 1174333 の反応式
[CH2:1]([C@H:8]1[C@H:12]([CH2:13][CH:14]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[O:11][C:10]([CH3:35])([CH3:34])[N:9]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:43][C:44]1[CH:45]=[CH:46][C:47]([Sn](CCCC)(CCCC)CCCC)=[N:48][CH:49]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C@H:8]1[C@H:12]([CH2:13][CH:14]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:47]3[CH:46]=[CH:45][C:44]([CH3:43])=[CH:49][N:48]=3)=[CH:18][CH:17]=2)[O:11][C:10]([CH3:35])([CH3:34])[N:9]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 67406532tert-butyl (4S,5S)-4-benzyl-5-[2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

生成物 1

HCID 67407093tert-butyl (4S,5S)-4-benzyl-5-{2-{[(benzyloxy)carbonyl]amino}-3-[4-(5-methyl-2-pyridinyl)phenyl]propyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate収率 63.5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A solution containing the product from Example 128B (0.50 g, 0.78 mmol) in DMF (8 mL) was treated with dichlorobis(triphenylphosphine)palladium(II) (0.165 g, 0.235 mmol), and the product from Example 74A (0.60 g, 1.63 mmol), stirred at 100° C. for 6 hours, cooled to 25° C., filtered through celite®, and partitioned between ethyl acetate and water. The organic was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-15% ethyl acetate in chloroform to give the product (0.322 g, 63% yield).

後処理

  1. filtrationfiltered through celite®
  2. custompartitioned between ethyl acetate and water
  3. washThe organic was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 0-15% ethyl acetate in chloroform

出典と根拠

ORDレコード
ord-f9d0603e86434099ab357f965bf24485
出典データセット
uspto-grants-2010_11
特許番号
US07834043B2

反応ノート

読み込み中…