Diethylamine → HCID 59596674, 화합물

HRID 2264815노트

반응식

HRID 2264815 반응식
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]#[CH:16])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])[CH3:3].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][NH:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1.C(NCC)C>[Cu]I.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.C(OCC)(=O)C>[CH3:4][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]#[C:16][C:29]1[CH:28]=[CH:27][C:26]([NH:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[F:17])=[CH:31][CH:30]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:1])[CH3:3]

참가 물질

7

반응물 3

HCID 8021DiethylamineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoateHCID 28878728HCID 28878728, 화합물

생성물 1

HCID 59596674HCID 59596674, 화합물수율 28.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D64, 365 mg, 1.60 mmol), prepared with analogous procedure to that described hereinabove, N-[(2-fluorophenyl)methyl]-4-iodoaniline (D63, 630 mg, 1.92 mmol) and diethylamine (0.82 ml, 585 mg, 8 mmol) was added CuI (30 mg, 0.08 mmol) and PdCl2(PPh3)2 (56 mg, 0.08 mmol). After stirring at room temperature for 5 h ethyl acetate was added and the solution was extracted with sat. ammonium chloride solution. The organic layer was dried (Na2SO4), filtered and evaporated. The resulting crude material was purified by flash chromatography using a cyclohexanes, ethyl acetate gradient (5%40%) on silica gel to afford the title compound (192 mg, 28%); UPLC: 0.88 min, MS: (ES/+) m/z: 427 [MH]+, C24H27FN2O4 requires 426.

후처리

  1. additionwas added
  2. extractionthe solution was extracted with sat. ammonium chloride solution
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting crude material was purified by flash chromatography

출처 및 근거

ORD 기록
ord-564ca925f9bd422d8d91752fd767705f
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855218B2

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