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Sodium Iodide → N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester

HRID 1110254
ノート
印刷プレビュー

反応式

HRID 1110254 の反応式
[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]=[C:11]([NH2:34])[CH:10]=1.Br[CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39].CN(C)[C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][C:58]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:42]1([CH2:41][O:40][C:38](=[O:39])[CH2:37][N:34]([C:11]2[CH:10]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:35])[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]=2)[CH2:4][C:3](=[O:2])[O:35][CH2:50][C:59]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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 543104535-[3-Amino-5-(octadecyloxy)phenoxy]pentanoic acid methyl ester

生成物 1

HCID 19388929N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester収率 120.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 6.77 g (13.8 mmol) of 5-[3-amino-5-(octadecyloxy)phenoxy]pentanoic acid methyl ester, 6.6 ml (41.3 mmol) of benzyl bromoacetate, 7.4 g (34.4 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.6 g (3.9 mmol) of sodium iodide in 150 ml of acetonitrile and 50 ml of DMF was stirred at reflux under an argon atmosphere for 48 hours. The reaction mixture was concentrated at reduced pressure to remove the solvents and ethyl acetate was added to the residue. The extract was washed with 0.5N HCl, with NaHCO3 solution, dried and concentrated at reduced pressure to an oil. Purification by HPLC using 20% ethyl acetate-hexane gave 6.55 g (60% yield, mp 48°-50°) of N-[3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

後処理

  1. temperatureat reflux under an argon atmosphere for 48 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customto remove the solvents and ethyl acetate
  4. additionwas added to the residue
  5. washThe extract was washed with 0.5N HCl, with NaHCO3 solution
  6. customdried
  7. concentrationconcentrated at reduced pressure to an oil
  8. customPurification by HPLC

出典と根拠

ORDレコード
ord-743ab6af07614aad86a6797976b4985b
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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