Hydrochloric Acid → N-Boc sphingosine

HRID 419761ノート

反応式

HRID 419761 の反応式
[OH:1][CH2:2][C@H:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C@H:4]([OH:20])[C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1(C)C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>C1COCC1>[C:24]([O:23][C:22]([NH:21][C@H:3]([C@@H:4](/[CH:5]=[CH:6]/[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[OH:20])[CH2:2][OH:1])=[O:28])([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 10834640HCID 10834640、化合物HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

生成物 1

HCID 10949378N-Boc sphingosine収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

The tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 0.21 mmol) obtained in the above-described reaction was dissolved in THF (21 ml) and cooled to 0° C.; a 65% toluene solution of sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) (258 μl, 0.850 mmol) was subsequently added dropwise. The resulting mixture was heated to room temperature and stirred for 2.5 hours. 1 M hydrochloric acid was subsequently added to the mixture, and the reaction was stopped; the mixture was extracted with diethylether, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to produce N-tert-butoxycarbonyl sphingosine (52 mg, 64%).

後処理

  1. temperatureThe resulting mixture was heated to room temperature
  2. extractionthe mixture was extracted with diethylether
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f41fee3654bd496bb9223df415f5ee13
出典データセット
uspto-grants-2012_01
特許番号
US08093395B2

反応ノート

読み込み中…