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Sodium Iodide → N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester

HRID 1110226
ノート
印刷プレビュー

反応式

HRID 1110226 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=1.Br[CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].CN(C)[C:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][C:54]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:38]1([CH2:37][O:36][C:34](=[O:35])[CH2:33][N:1]([C:2]2[CH:3]=[C:4]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=2)[CH2:33][C:34](=[O:35])[O:36][CH2:46][C:55]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19389144N,N'-(5-amino-1,3-phenylene)bisdecanamide

生成物 1

HCID 19389157N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester収率 20%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 6342Acetonitrile溶媒

実験手順

A mixture of 1.92 g (4.45 mmol) of N,N'-(5-amino-1,3-phenylene)bisdecanamide, 10.6 ml (0.061 mol) of benzyl bromoacetate, 2.4 g (11.1 mmol) of 1,8-bis(dimethylamino)-naphthalene and 0.19 g (1.25 mmol) of sodium iodide in 50 ml of acetonitrile and 15 ml of DMF was stirred and refluxed under an argon atmosphere for 36 hours. The solvents were removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with 0.05N HCl, with NaHCO3 solution, dried and concentrated to a brown solid. Purification by HPLC using 25% ethyl acetate-hexane gave 0.9 g which was recrystallized from acetone-hexane to give 0.064 g (20% yield, mp 127°-129°) of N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

後処理

  1. temperaturerefluxed under an argon atmosphere for 36 hours
  2. customThe solvents were removed at reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe extract was washed with 0.05N HCl, with NaHCO3 solution
  5. customdried
  6. concentrationconcentrated to a brown solid
  7. customPurification by HPLC
  8. customgave 0.9 g which
  9. customwas recrystallized from acetone-hexane

出典と根拠

ORDレコード
ord-29f3638f7aa845eb9e712a515d81e539
出典データセット
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05324747

反応ノート

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