Acetic Anhydride → 6,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrile

HRID 1109847ノート

反応式

HRID 1109847 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][N:16]([C:23](=[O:52])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1.C(Cl)Cl>[CH2:8]([O:15][N:16]([C:23](=[O:52])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][N:34]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:1](=[O:3])[CH3:2])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 99862666,12,18-Tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile

生成物 1

HCID 101008386,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrile収率 60%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Acetic anhydride (8 mL) was slowly added to a solution of (8) (1.25 g, 2.03 mmol) in pyridine (50 mL) and CH2Cl2 (30 mL) which had been cooled to 0° C. Stirring was continued at 0° C. for 30 minutes and then at room temperature overnight. Solvents were removed under high vacuum, and the residue was dissolved in CHCl3 (120 mL), followed by washing with 0.5N HCl (2×40 mL) and saturated NaHCO3 (2×40 mL). After solvent removal, the crude oil was purified by silica gel column chromatography, eluting with 3:1 EtOAc/hexane, to furnish 0.8 g (60%) of (9) as an oil: NMR δ 1.40-1.80 (m, 12 H), 2.05 (s, 3 H), 2.20-2.50 (m, 6 H), 3.40-3.73 (m, 6 H), 4.75 (s, 6 H) , 7.32 (s, 15 H). Anal. (C38H48N4O6) C, H, N.

後処理

  1. customat room temperature
  2. customovernight
  3. customSolvents were removed under high vacuum
  4. dissolutionthe residue was dissolved in CHCl3 (120 mL)
  5. washby washing with 0.5N HCl (2×40 mL) and saturated NaHCO3 (2×40 mL)
  6. customAfter solvent removal
  7. customthe crude oil was purified by silica gel column chromatography
  8. washeluting with 3:1 EtOAc/hexane

出典と根拠

ORDレコード
ord-215dcef00ec74818b619f710d9eaf4cb
出典データセット
uspto-grants-1994_06
特許番号
US05322961

反応ノート

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