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Triethylamine → 3-methoxy-2-(N-methyl-octadecylamino)-propanol phosphocholine

HRID 1197161
ノート
印刷プレビュー

反応式

HRID 1197161 の反応式
[CH3:1][O:2][CH2:3][CH:4]([N:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:8])[CH2:5][OH:6].[CH2:27](N(CC)CC)C.Cl[P:35]1(=[O:40])[O:39]CC[O:36]1>C1C=CC=CC=1>[P:35]([O:6][CH2:5][CH2:4][N+:7]([CH3:9])([CH3:27])[CH3:8])([OH:40])([OH:39])=[O:36].[CH3:1][O:2][CH2:3][CH:4]([N:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:8])[CH2:5][OH:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 810872-Chloro-1,3,2-dioxaphospholane 2-oxideHCID 198978403-methoxy-2-(N-methyl-octadecylamino)propanol

生成物 1

HCID 867458643-methoxy-2-(N-methyl-octadecylamino)-propanol phosphocholine収率 39%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

反応条件

温度
5 °C

実験手順

Compound of the formula Ia wherein R1 =CH3, R2 =C18H37, R3 =CH3, ##STR12## 2 g (5 mmol) of 3-methoxy-2-(N-methyl-octadecylamino)propanol (IIa) and 3 ml of triethylamine were dissolved in 20 ml of dry benzene, and the mixture was cooled to 5° C. under nitrogen circulation. 1 g (7 mmol) of 2-chloro-2-oxo-1,3,2-dioxaphospholane in 4 ml of benzene was added under stirring, and stirring was continued overnight. The amino salt was filtered off and washed with benzene. The filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in 20 ml of dry methyl cyanide and transferred to a reactor. 20 ml of methyl cyanide, saturated with gaseous trimethylamine, was added, and the mixture was heated at 65° C. for 24 hours. A solid separated on cooling. It was filtered off and chromatographed on silica gel (eluent chloroform:methanol 90:10, then 70:30 by volume, then methanol) to yield 1.1 g (39%) of the title compound.

後処理

  1. stirringstirring
  2. filtrationThe amino salt was filtered off
  3. washwashed with benzene
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in 20 ml of dry methyl cyanide
  6. customtransferred to a reactor
  7. addition20 ml of methyl cyanide, saturated with gaseous trimethylamine, was added
  8. temperaturethe mixture was heated at 65° C. for 24 hours
  9. customA solid separated
  10. temperatureon cooling
  11. filtrationIt was filtered off
  12. customchromatographed on silica gel (eluent chloroform:methanol 90:10

出典と根拠

ORDレコード
ord-a498470fd4a24a8689218fa5a7b6b689
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05116992

反応ノート

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