Water → HCID 68683629, 화합물

HRID 1713801노트

반응식

HRID 1713801 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 68683629HCID 68683629, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a662f939efc54032a8cc040008ab7831
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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