Ethyl bromoacetate → [2-(2-Methanesulfonylamino-ethyl)-phenoxy]-acetic Acid Ethyl Ester

HRID 1699021ノート

反応式

HRID 1699021 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>O.CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:43]

参加物

7

反応物 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 22246821N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide

生成物 1

HCID 53987382[2-(2-Methanesulfonylamino-ethyl)-phenoxy]-acetic Acid Ethyl Ester収率 13.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide (4.3 g, 20 mmol), Nal (1.2 g, 8.0 mmol), K2CO3 (6.07 g, 44 mmol), ethyl bromoacetate (3.34 g, 20 mmol), and DMF (70 mL) was stirred at room temperature for 24 h. The reaction was poured into water and the aqueous solution was extracted with CH2Cl2. The organic solution was washed with water (1×) followed by brine (1×). The organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (hexanes to 7:3 hexanes:EtOAc) provided the title compound (800 mg). 1H NMR (400 MHz, CDCl3) δ7.18 (m, 2H), 6.93 (t, 1H), 6.71 (d, 1H), 4.97 (m, 1H), 4.65 (s, 2H), 4.24 (q, 2H), 3.42 (m, 2H), 2.94 (t, 2H), 2.75 (s, 3H), 1.27 (t, 3H); MS 319 (M+18).

後処理

  1. extractionthe aqueous solution was extracted with CH2Cl2
  2. washThe organic solution was washed with water (1×)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-86a1f4fcf65a4dbba694763929d91f57
出典データセット
uspto-grants-2002_02
特許番号
US06344485B1

反応ノート

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