Water → HCID 68683629、化合物

HRID 1713801ノート

反応式

HRID 1713801 の反応式
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].Cl.[O:9]([CH2:16][CH2:17][CH2:18][NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1.O>C(Cl)Cl>[O:7]=[C:2]([NH:19][CH2:18][CH2:17][CH2:16][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 18590545(3-Aminopropoxy)benzene hydrochloride

生成物 1

HCID 68683629HCID 68683629、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl chloro(oxo)acetate (1.77 mL) was added to a stirred solution of (3-phenoxypropyl)amine hydrochloride (3000 mg) and pyridine (2.98 mL) in DCM (100 mL) at 0° C. After the addition was complete the solution was allowed to warm to ambient temperature and stirred for 16 hours. Water (50 mL) was added and the mixture was extracted with DCM (2×75 mL). The organic extracts were combined, washed with brine (50 mL), dried and concentrated in vacuo to give an oil. This was purified by flash chromatography on a 90 g Biotage™ silica column using a gradient of 10-60% EtOAc in hexane as the eluent to give methyl oxo[(3-phenoxypropyl)amino]acetate (3212 mg) as a solid; 1H NMR δ (CDCl3) 7.60 (1H, bs), 7.28 (2H+CHCl3, m), 6.94 (3H, m), 4.07 (2H, t), 3.90 (3H, s), 3.58 (2H, quartet), 2.08 (2H, m), +0.1 mole of EtOAc; MS m/e MH+ 238.

後処理

  1. additionAfter the addition
  2. extractionthe mixture was extracted with DCM (2×75 mL)
  3. washwashed with brine (50 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on a 90 g Biotage™ silica column

出典と根拠

ORDレコード
ord-a662f939efc54032a8cc040008ab7831
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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