1,2-Dichloroethane → Ethyl 3-{[[4-(benzyloxy)butyl](propyl)amino]carbonyl}-5-methylbenzoate

HRID 1350996노트

반응식

HRID 1350996 반응식
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([CH3:31])[CH:30]=1)[C:25]([OH:27])=O)=[O:21])[CH3:18].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH3:16])[C:25]([C:24]1[CH:23]=[C:22]([CH:30]=[C:29]([CH3:31])[CH:28]=1)[C:20]([O:19][CH2:17][CH3:18])=[O:21])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 210858303-(Ethoxycarbonyl)-5-methylbenzoic acidHCID 21087152N-[4-(benzyloxy)butyl]-N-propylamine

생성물 1

HCID 21086098Ethyl 3-{[[4-(benzyloxy)butyl](propyl)amino]carbonyl}-5-methylbenzoate수율 41.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of N-[4-(benzyloxy)butyl]-N-propylamine (2.31 g, 10.44 mmol), 3-(ethoxycarbonyl)-5-methylbenzoic acid (2.18 g, 10.44 mmol), HOBt (1.56 g, 11.49 mmol), N-methylmorpholine (1.37 mL, 12.52 mmol), and EDC (2.20 g, 11.49 mmol) in DMF (12 mL) is stirred at 20–25 degrees C. for 18 hours. The reaction mixture is diluted with ethyl acetate (80 mL) and washed with water (2×20 mL), hydrochloric acid (1 N, 20 mL), saturated sodium bicarbonate (20 mL) and saline (20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by flash chromatography (silica; hexanes/ethyl acetate,1/1) gives ethyl 3-{[[4-(benzyloxy)butyl](propyl)amino]carbonyl}-5-methylbenzoate (1.79 g), NMR (500 MHz, DMSO-d6): delta7.80, 7.64, 7.40, 7.38–7.16, 4.50–4.43, 4.34–4.29, 3.53–3.30, 3.20–3.06, 2.41–2.36, 1.70–1.40, 1.36–1.29, 0.94–0.84 and 0.82–0.72; APCI-MS (m/z) [M+H]+=412.

후처리

  1. washwashed with water (2×20 mL), hydrochloric acid (1 N, 20 mL), saturated sodium bicarbonate (20 mL) and saline (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (silica; hexanes/ethyl acetate,1/1)

출처 및 근거

ORD 기록
ord-699d1acbf5f84c43ab03dad88f2b509a
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214715B2

반응 노트

불러오는 중…