2-Naphthylamine → Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 2-naphthyl-amide

HRID 1067083ノート

反応式

HRID 1067083 の反応式
[CH2:1]([N:8]([CH3:24])[C@H:9]([C:21]([OH:23])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:67][C:68]1[CH:77]=[CH:76][C:75]2[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=2)[CH:69]=1>C(OCC)(=O)C.O1CCCC1>[CH:69]1[C:70]2[C:75](=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:76]=[CH:77][C:68]=1[NH:67][C:21](=[O:23])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:24]

参加物

7

反応物 4

HCID 70572-NaphthylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 57299805Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine

生成物 1

HCID 86757006Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 2-naphthyl-amide収率 68.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of Nα-benzyl-Nδ-Boc-Nα-methylornithine (2.13 g, 6.3 mmol), diisopropyl-ethylamine (2.2 ml, 12.6 mmol), and anhydrous tetrahydrofuran (20 ml) was treated with PyBop (4 g, 7.6 mmol) at 0° C. for 10 min., followed by the addition of β-amino-naphthalene (1.09 g, 7.6 mmol). The resulting solution was stirred at ambient temperature overnight, and the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by silica gel chromatography (hexane/ethyl acetate) to afford Nα-benzyl-Nδ-Boc-Nα-methylornithine 2-naphthyl-amide (2 g): 1H NMR (400 MHz, CDCl3) δ1.43 (s, 9H), 1.6-1.9 (m, 4H), 2.38 (s, 3H), 3.2-3.3 (m, 2H), 3.7-3.8 (m, 2H), 4.7 (s, 1H), 7.25-7.8 (m, 11H), and 8.25 (s, 1H).

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by silica gel chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-ffcc695df24e44fe98a8f93003153425
出典データセット
uspto-grants-2001_06
特許番号
US06245746B1

反応ノート

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