Nitrogen → (2S,3R)-Methyl 2-(4-((4-formylphenyl)ethynyl)benzamido)-3-hydroxybutanoate

HRID 1692518노트

반응식

HRID 1692518 반응식
[OH:1][C@H:2]([CH3:25])[C@H:3]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14](C(C2C=CC=CC=2)=O)=[CH:13][CH:12]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].C(OC(NCC(N[C:38]1[CH:43]=[CH:42]C(I)=[CH:40][CH:39]=1)=O)=O)(C)(C)C.CCN(CC)CC.N#N.[CH2:54]1[CH2:58][O:57][CH2:56][CH2:55]1>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.[Cu]I>[CH3:7][O:6][C:4](=[O:5])[C@@H:3]([NH:8][C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([C:42]#[C:43][C:38]2[CH:56]=[CH:55][C:54]([CH:58]=[O:57])=[CH:40][CH:39]=2)=[CH:13][CH:12]=1)[C@H:2]([OH:1])[CH3:25]

참가 물질

8

반응물 5

HCID 947NitrogenHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 474512392-[(tert-butoxy)carbonylamino]-N-(4-iodophenyl)acetamideHCID 59697585methyl(2S,3R)-3-hydroxy-2-{[4-(phenylcarbonyl)phenyl]carbonylamino}butanoate

생성물 1

HCID 59697530(2S,3R)-Methyl 2-(4-((4-formylphenyl)ethynyl)benzamido)-3-hydroxybutanoate수율 80%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

실험 절차

A solution of alkyne 1 (745 mg, 2.85 mmol), 4-iodobenzaldehyde 2 (902 mg, 3.89 mmol), and Et3N (900 μL, 6.5 mmol) in THF (50 mL) was purged with a stream of N2 for two minutes and then treated with PdCl2(PPh3)2 (70 mg, 0.10 mmol) and CuI (34 mg, 0.18 mmol). The reaction mixture was stirred 40 h, concentrated by rotary evaporation and purified by silica gel chromatography (40:1 DCM/MeOH) to give 0.833 g (80% yield) of (2S,3R)-2-[4-(4-formyl-phenylethynyl)-benzoylamino]-3-hydroxy-butyric acid methyl ester 3 as a pale yellow powder, mp=143-144° C. Rf=0.3 (25:1 DCM/MeOH); LRMS (ES+) m/z 366.1 (C21H19NO5+H requires 366.13); HPLC (300 nm, 47 min) 15.3 min.

후처리

  1. concentrationconcentrated by rotary evaporation
  2. custompurified by silica gel chromatography (40:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-fcbae179af35405ea597f969f4158c40
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153843B2

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