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Ethyl Acetate → HCID 58631154、化合物

HRID 525607
ノート
印刷プレビュー

反応式

HRID 525607 の反応式
C(OCC)(=O)C.[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[O:19][C:18]([CH3:21])([CH3:20])[N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@@H:16]2[CH2:29][F:30])=[CH:11][CH:10]=1)#[CH:8].Cl/[C:32](=[N:38]/[OH:39])/[C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:25]([O:24][C:22]([N:17]1[C@H:16]([CH2:29][F:30])[C@@H:15]([C:12]2[CH:11]=[CH:10][C:9]([C:7]3[O:39][N:38]=[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:8]=3)=[CH:14][CH:13]=2)[O:19][C:18]1([CH3:21])[CH3:20])=[O:23])([CH3:28])([CH3:27])[CH3:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 58631078HCID 58631078、化合物

生成物 1

HCID 58631154HCID 58631154、化合物収率 31.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

To an ethyl acetate (20 ml) solution of (4S,5R)-tert-butyl 5-(4-ethynylphenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate (1.35 g, 4.0 mmol) is added a dimethylformamide solution of (E)-ethyl 2-chloro-2-(hydroxyimino)-acetate (12.5 ml, 1.5 g, 2.5 equiv). Sodium hydrogen carbonate (3.5 g) is added to the solution and it is allowed to stir overnight at room temperature. The mixture is filtered and diluted with ethyl acetate (100 ml). After washing with water (4×25 ml) the organic phase is concentrated to give the crude product, which is purified on silica gel using a gradient of ethyl acetate in hexanes (0% to 20% ethyl acetate) to give the title compound (567 mg): 1H NMR (400 MHz, CDCl3) 1.43-1.56 (m, 14 H) 1.62 (s, 3 H) 1.74 (br. s., 3 H) 4.50 (q, J=7.24 Hz, 3 H) 5.20 (d, J=7.33 Hz, 1 H) 6.96 (s, 1 H) 7.60 (d, J=8.34 Hz, 2 H) 7.86 (d, J=8.59 Hz, 2 H), m/z (Cl) 449 ([M+H]+.

後処理

  1. filtrationThe mixture is filtered
  2. additiondiluted with ethyl acetate (100 ml)
  3. washAfter washing with water (4×25 ml) the organic phase
  4. concentrationis concentrated
  5. customto give the crude product, which
  6. customis purified on silica gel using a gradient of ethyl acetate in hexanes (0% to 20% ethyl acetate)

出典と根拠

ORDレコード
ord-3e99a78dfd7f4fdb9f47275d02a10d8b
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340564B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート