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Dichloromethane → tert-Butyl(3S)-3-(tert-butoxycarbonylamino)-5-(2-methyl-5-nitro-phenyl)pent-4-enoate

HRID 1053663
ノート
印刷プレビュー

反応式

HRID 1053663 の反応式
[I-].[C:2]([O:6][C:7](=[O:38])[CH2:8][C@H:9]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:5])([CH3:4])[CH3:3].[CH3:39][C:40]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][C:41]=1[CH:42]=O.C(Cl)Cl.CC(C)([O-])C.[K+]>O1CCCC1.O=[Mn]=O>[C:34]([O:33][C:31]([NH:30][C@H:9]([CH:10]=[CH:42][C:41]1[CH:44]=[C:45]([N+:48]([O-:50])=[O:49])[CH:46]=[CH:47][C:40]=1[CH3:39])[CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:38])=[O:32])([CH3:37])([CH3:36])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 126541452-Methyl-5-nitrobenzaldehydeHCID 23665647Potassium tert-butoxideHCID 118276603[(2S)-4-tert-Butoxy-2-(tert-butoxycarbonylamino)-4-oxo-butyl]-triphenyl-phosphonium iodide

生成物 1

HCID 118276704tert-Butyl(3S)-3-(tert-butoxycarbonylamino)-5-(2-methyl-5-nitro-phenyl)pent-4-enoate

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Adapting a literature procedure (Jandeleit et al., U.S. Pat. No. 8,168,617 (2012)), tert-butyl(3S)-3-(tert-butoxycarbonylamino)-5-(2-methyl-5-nitro-phenyl)pent-4-enoate (18b) is prepared from [(2S)-4-tert-butoxy-2-(tert-butoxycarbonylamino)-4-oxo-butyl]-triphenyl-phosphonium iodide (18a) (1.30 g, 2.0 mmol), 2-methyl-5-nitro-benzaldehyde (1b) (495 mg, 3.0 mmol) (commercial or prepared in two steps from commercial 2-methyl-5-nitro benzoic acid (i) BH3.SMe2, THF, reflux, ii) MnO2, DCM, room temperature) as described in Example 1) with a commercial ˜1.0 M solution of potassium tert-butoxide (KOtBu) (3.0 mL, 3.0 mmol) in anhydrous tetrahydrofuran (THF) (10 mL) at with gradual warming from 0° (ice bath) to room temperature for 24 hours. Aqueous work and purification by silica gel column chromatography furnish the title compound (18b) as a mixture of geometric isomers ((E)/(Z)-isomers).

後処理

  1. customAqueous work and purification by silica gel column chromatography

出典と根拠

ORDレコード
ord-a2fc7e2752dc40c1a1b7ddb0d5f5892f
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394237B2

反応ノート

読み込み中…

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