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 1174333노트

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HRID 1174333 반응식
[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

참가 물질

5

반응물 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

생성물 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-carboxylate수율 63.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f9d0603e86434099ab357f965bf24485
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834043B2

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