1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid methyl ester

HRID 849834노트

반응식

HRID 849834 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[CH3:31][O:32][C:33](=[O:47])[C@@H:34]([CH2:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=1)[NH2:35]>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C>[CH3:31][O:32][C:33](=[O:47])[C@H:34]([NH:35][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:11]=1)[CH2:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=1

참가 물질

7

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559293-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 7016520(R)-Methyl 2-amino-3-(naphthalen-2-yl)propanoate

생성물 1

HCID 53653839(R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid methyl ester수율 90.8%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

3-(tert-Butoxycarbonylaminomethyl)benzoic acid (5.32 g; 21.2 mmol) was dissolved in N,N-dimethylformamide (20 ml). 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (4.06 g, 21.2 mmol) was added and the mixture was stirred for 20 min. A solution of (R)-3-(2-naphthyl)alanine methyl ester (4.85 g, 21.2 mmol) in N,N-dimethylformamide (20 ml) and triethylamine (4.4 ml) was added and stirring was continued for 18 h. The mixture was diluted with ethyl acetate (400 ml) and the organic phase was washed with water (200 ml), 10% aqueous sodium hydrogensulfate (50 ml), 5% aqueous sodium hydrogencarbonate (100 ml) and water (100 ml). The phases were separated and the organic phase was dried (magnesium sulfate) and the solvent removed in vacuo to afford 8.9 g of (R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid methyl ester.

후처리

  1. stirringstirring
  2. waitwas continued for 18 h
  3. washthe organic phase was washed with water (200 ml), 10% aqueous sodium hydrogensulfate (50 ml), 5% aqueous sodium hydrogencarbonate (100 ml) and water (100 ml)
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried (magnesium sulfate)
  6. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-d6d198ff8cd64ff68c749e389cdaba03
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06013658

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