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

HRID 1692518ノート

反応式

HRID 1692518 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fcbae179af35405ea597f969f4158c40
出典データセット
uspto-grants-2012_04
特許番号
US08153843B2

反応ノート

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