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1,2-Dichloroethane → N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester

HRID 1292676
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HRID 1292676 반응식
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([OH:16])=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:20][O:21][C:22](=[O:43])[CH2:23][N:24]([CH2:36][C@@H:37]([NH2:42])[C@@H:38]([CH3:41])[CH2:39][CH3:40])[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH3:20][O:21][C:22](=[O:43])[CH2:23][N:24]([CH2:36][C@@H:37]([NH:42][C:14](=[O:16])[CH2:13][C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:18][CH:17]=2)[CH:9]=[N:10][CH:11]=1)[C@@H:38]([CH3:41])[CH2:39][CH3:40])[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 184336301-(4-Cyanobenzyl)imidazole-5-acetic acidHCID 70338221N-[2(S)-(amino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester hydrochloride

생성물 1

HCID 67572382
N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid (220 mg, 0.533 mmol) and the amine hydrochloride salt from step C (212 mg, 0.533 mmol), HOBT (72 mg, 0.533 mmol), and N-methylmorpholine (117 μl, 1.11 mmol) in DMF (2 ml) was added EDC (764 mg, 3.99 mmol). The reaction was stirred at room temperature for 72 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine, dried (Na2SO4). and evaporated in vacuo. The residue was chromatographed (SiO2, 3-4% MeOH in CH2Cl2, gradient elution) to afford the title compound as a white solid.

후처리

  1. washthe organic layer washed with sat. aq NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customand evaporated in vacuo
  4. customThe residue was chromatographed
  5. wash(SiO2, 3-4% MeOH in CH2Cl2, gradient elution)

출처 및 근거

ORD 기록
ord-9223f5ea085644d2b537113073957443
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05756528

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