tert-Butyl cyanoacetate → Tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate

HRID 1767369노트

반응식

HRID 1767369 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=O)[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[NH:23][C@H:24]([CH:34]=O)[C:25](=C=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(C)(C)C.[C:36]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])#[N:37].[C:46]([O-:49])(=[O:48])C.[NH4+:50]>COCCOC>[NH2:37][C:36]1[NH:50][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:34]([CH:24]([NH:23][C:46]([O:49][C:2]([CH3:7])([CH3:3])[CH3:1])=[O:48])[CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:38]=1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]

참가 물질

6

반응물 4

HCID 70693tert-Butyl cyanoacetateHCID 517165Ammonium AcetateHCID 5205131-[2-(Benzyloxy)phenyl]ethan-1-oneHCID 86604947N-tert-butoxy-carbonyl-phenylalaninal

생성물 1

HCID 22258838Tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate수율 32.3%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of the starting compound 1A (3.000 g, 13.258 mmol), N-tert-butoxy-carbonyl-phenylalaninal (3.305 g, 13.258 mmol), tert-butyl cyanoacetate (1.872 g, 13.258 mmol), ammonium acetate (3.066 g, 39.774 mmol) and 1,2-dimethoxyethane (5.0 mL) was heated at reflux for 6 hrs. After cooled to room temperature, the mixture was extracted with ethyl acetate and saturated NaHCO3 solution. The separated organic phase was washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with diisopropyl ether to give tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate as a yellow solid (1.281 g, yield; 16%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs
  3. extractionthe mixture was extracted with ethyl acetate and saturated NaHCO3 solution
  4. washThe separated organic phase was washed with water and brine successively
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether

출처 및 근거

ORD 기록
ord-66f6518548ac41a2b2220e9731489a0e
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232909B2

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