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

HRID 1701025ノート

反応式

HRID 1701025 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-704a3d2581224768b82c26d8bf3119e3
出典データセット
uspto-grants-2002_02
特許番号
US06350767B1

反応ノート

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