1,2-Dichloroethane → HCID 15951585, 화합물

HRID 1642258노트

반응식

HRID 1642258 반응식
[C:1]([NH:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]([OH:9])=O)(=[O:3])[CH3:2].C(Cl)CCl.C(N(CC)CC)C.[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[NH2:39])=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:27][C:28]1[CH:41]=[CH:40][C:31]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[NH:39][C:7](=[O:9])[CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:30][CH:29]=1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 760102-(4-Chlorophenoxy)anilineHCID 34808823-Acetamido-3-phenylpropanoic acid

생성물 1

HCID 15951585HCID 15951585, 화합물수율 31.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a pre-stirred solution of N-acetyl-3-phenyl-β-alanine (104 mg, 0.50 mmol), EDC (265 mg, 1.38 mmol), triethylamine (70 mg, 0.69 mmol) and DMAP (6 mg, 0.046 mmol) in anhydrous DCM (25 ml), was added 2-(4-chlorophenoxy)phenylamine (100 mg, 0.46 mmol). This mixture was then allowed to stir at room temperature for 14 h. The reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml) and the organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH) then proceeded to afford the desired product as an off-white solid (58.9 mg, 31%). 1H NMR (270 MHz, CDCl3): δ 2.03 (3H, s, CH3), 2.83-2.99 (2H, m, CH2), 5.30-5.40 (1H, m, CH), 6.73-6.77 (1H, dd, J=1.5, 8.2 Hz, Ar—H), 6.83-6.86 (2H, m, Ar—H), 6.95-7.03 (1H, td, J=1.7, 7.9 Hz, Ar—H), 7.05-7.11 (1H, td, J=1.7, 7.9 Hz, Ar—H), 7.19-7.30 (7H, m, Ar—H), 7.60 (1H, br s, Ar—H), 8.22-8.25 ppm (1H, dd, J=1.5, 8.0 Hz, Ar—H). LCMS: M+H, 409.44 HPLC: 98.66% (2.268 mins, isocratic 90% acetonitrile, 10% water at 1 ml/min).

후처리

  1. washThe reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml)
  2. dry with materialthe organics were then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH)

출처 및 근거

ORD 기록
ord-fb98fe3ef37e47e7a1c0c7aab291c9be
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119627B2

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