Ethyl Acetate → 3-[4-(Hydroxyimino-methyl)-phenyl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 1961548ノート

反応式

HRID 1961548 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+].C(OCC)(=O)C>C(O)C.O.CCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[N:21][OH:22])=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21250649HCID 21250649、化合物

生成物 1

HCID 766614793-[4-(Hydroxyimino-methyl)-phenyl]-azetidine-1-carboxylic acid tert-butyl ester収率 94.51%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 19096565Water ethanol溶媒

実験手順

To a stirred suspension of 3-(4-Formyl-phenyl)-azetidine-1-carboxylic acid tert-butyl ester (Preparation 38, 6.5 g, 24.904 mmol, 1 equivalents) in ethanol:water (1:1, 120 mL) was added hydroxylamine hydrochloride (2.5 g, 37.356 mmol, 1.5 equivalents) followed by sodium acetate (3.67 g, 44.82 mol, 1.8 eq). Resulting reaction mixture was stirred at room temperature for 0.5 hours. Progress of the reaction was monitored by TLC using 20% ethyl acetate in hexane and visualized in UV light (254 nm). Reference of new spot and starting material was 0.32 and 0.67 respectively. After consumption of starting material, solvents was evaporated under reduced pressure and extracted with DCM (3×25 mL). Evaporation of volatiles provided light yellow solid (6.5 g, 94.51%). LC-MS and 1H NMR was consistent. 1H NMR (400 MHz, DMSO-d6) δ 1.39 (s, 9H), 3.81 (broad s, 3H), 4.42 (broad s, 2H), 7.36 (d, J=8 Hz, 2H), 7.57 (d, J=8 Hz, 2H), 8.12 (s, 1H), 11.19 (s, 1H). LC-MS (m/z):=277.30 (M+H).

後処理

  1. customResulting
  2. customreaction mixture
  3. customAfter consumption of starting material, solvents
  4. customwas evaporated under reduced pressure
  5. extractionextracted with DCM (3×25 mL)
  6. customEvaporation of volatiles

出典と根拠

ORDレコード
ord-d96e0417563441b2ae4f930a387c8743
出典データセット
uspto-grants-2013_04
特許番号
US08415310B2

反応ノート

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