1,2-Dichloroethane → N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline Methyl Ester

HRID 1292057노트

반응식

HRID 1292057 반응식
[C:1]([NH:4][C@H:5]([C:14]([NH:16][C@H:17]([C:21]([OH:23])=O)[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[CH3:24][O:25][C:26](=[O:39])[C@@H:27]1[CH2:31][CH:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][NH:28]1.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C)C=O.C(OCC)(=O)C.ClCCl>[CH3:24][O:25][C:26](=[O:39])[C@@H:27]1[CH2:31][CH:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][N:28]1[C:21](=[O:23])[C@H:17]([CH:18]([CH3:19])[CH3:20])[NH:16][C:14](=[O:15])[C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2]

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22875497N-Acetyl-tyrosinyl-valineHCID 545742204-Phenoxyproline methyl ester

생성물 1

HCID 54377655N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline Methyl Ester수율 46.3%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

N-Acetyl-tyrosinyl-valine (0.524 g, 1.63 mmol) and 4-phenoxyproline methyl ester (0.381 g, 1.48 mmol) were dissolved in 4 ml each of dimethylformamide and dichloromethane and cooled to 0° C. To the cooled solution was added diisopropylethylamine (258 ul, 1.86 mmol), HOBT (0.24 g, 1.78 mmol), and EDC (0.37 g, 1.92 mmol) and the reaction was stirred for 18 hrs. The mixture was diluted with 400 ml of ethyl acetate and washed with water, 10% sodium hydrogen sulfate, 10% sodium bicarbonate, and water. The organic layer was concentrated to give a residue that was purified by flash chromatography (SiO2) eluting with 94:6:1 (CH2Cl2:i-PrOH:Pyridine) to afford 360 mg of the title compound.

후처리

  1. washwashed with water, 10% sodium hydrogen sulfate, 10% sodium bicarbonate, and water
  2. concentrationThe organic layer was concentrated
  3. customto give a residue that
  4. customwas purified by flash chromatography (SiO2)
  5. washeluting with 94:6:1 (CH2Cl2:i-PrOH:Pyridine)

출처 및 근거

ORD 기록
ord-9b665b496bb94213a9ebaa122a161bfc
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756466

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