Hydrochloric Acid → N-Boc sphingosine

HRID 419761노트

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HRID 419761 반응식
[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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 10834640HCID 10834640, 화합물HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

생성물 1

HCID 10949378N-Boc sphingosine수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f41fee3654bd496bb9223df415f5ee13
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093395B2

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