4-Chlorobenzaldehyde → N-(5-(4-cyanobenzyloxy)-2-(4-chlorobenzylamino)benzoyl)-b-alanine ethyl ester

HRID 1488706노트

반응식

HRID 1488706 반응식
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][NH:7][C:8](=[O:26])[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[NH2:25])[CH3:2].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C([SiH](CC)CC)C>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][NH:7][C:8](=[O:26])[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:10]=1[NH:25][CH2:33][C:32]1[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 77264-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 19700602HCID 19700602, 화합물

생성물 1

HCID 22905094N-(5-(4-cyanobenzyloxy)-2-(4-chlorobenzylamino)benzoyl)-b-alanine ethyl ester수율 59.5%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A solution of 1.03 g (2.80 mmol) of N-(5-(4-cyanobenzyloxy)-2-aminobenzoyl)-b-alanine ethyl ester, 394 mg (2.80 mmol) of p-chlorobenzaldehyde, and 20 mg of p-toluenesulfonic acid in 30 mL of toluene was heated at reflux through a Dean-Stark trap for 45 min. The solvent was removed in vacuo and the residue was dissolved in 15 mL of trifluoroacetic acid. Triethylsilane (1.34 mL, 8.40 mmol) was added and the mixture was stirred at room temperature for 12 h, concentrated in vacuo, and partitioned between 1N aqueous sodium bicarbonate and ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate, and concentrated. Chromatography (silica gel-60, 2:3 ethyl acetate/hexane) gave 820 mg (59%) of N-(5-(4-cyanobenzyloxy)-2-(4-chlorobenzylamino)benzoyl)-b-alanine ethyl ester as a colorless solid. 1H NMR (300 MHz, CDCl3) d 7.66 (2H, d, J=7.8 Hz, NC-Ar-H2), 7.51 (2H, d, J=7.8 Hz, NC-Ar-H2), 7.27 (4H, s, ClArH4), 6.98 (1H, d, J=2.0 Hz, O-Ar-H), 6.89 (1H, dd, J=2.0, 9.3 Hz, O-Ar-H), 6.78 (1H, b, N-H), 6.66 (1H, d, J=9.3 Hz, O-Ar-H), 5.03 (2H, s, ArCH2O), 4.32 (2H, s, ClArCH2), 4.17 (2H, q, J=7.3 Hz, OCH2CH3), 3.65 (2H, bq, J=5.7 Hz, NHCH2CH2), 2.62 (2H, t, J=5.7 Hz, NHCH2CH2), 1.28 (3H, t, J=7.3 Hz, OCH2 CH3); Exact mass (FAB, M+H+) calcd for C27H27 ClN3O4 : 492.1690; Found: 492.1681.

후처리

  1. temperatureat reflux through a Dean-Stark trap for 45 min
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 15 mL of trifluoroacetic acid
  4. concentrationconcentrated in vacuo
  5. custompartitioned between 1N aqueous sodium bicarbonate and ethyl acetate
  6. washThe organic phase was washed with water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b6f0ca7ef5484284866fcf76c4819599
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674863

반응 노트

불러오는 중…