Diisopropylcarbodiimide → Ceramide 1 A

HRID 1005616노트

반응식

HRID 1005616 반응식
[C:1]([O: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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=O)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].ON1C2C=CC=CC=2N=N1.[OH:60][CH2:61][C@@H:62]([C@@H:64]([C@@H:66]([CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[OH:67])[OH:65])[NH2:63].C(N=C=NC(C)C)(C)C>C(Cl)(Cl)Cl>[C:1]([O: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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([NH:63][C@H:62]([C@@H:64]([C@@H:66]([CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])[OH:67])[OH:65])[CH2:61][OH:60])=[O:49])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

6

반응물 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 122121PhytosphingosineHCID 8675418527-Linoleoyloxyheptacosanoic acid

생성물 1

HCID 73425489Ceramide 1 A수율 38.6%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
45 °C

실험 절차

A mixture of 27-linoleoyloxyheptacosanoic acid (5 g, 7.2 moles), chloroform (90 ml), dried 1-hydroxybenzotriazole (3.2 g, 27.3 mmoles), phytosphingosine (3.07 g, 9.7 mmoles) and N,N'-diisopropylcarbodiimide (2.2 ml, 14.1 mmoles) was stirred under nitrogen for 90 minutes at 45° C. and then overnight at room temperature. After washing with 50 ml of a 1N hydrochloric acid solution and brine and filtration the organic layer was concentrated. After addition of hot isopropanol (150 ml) the mixture was filtered while still hot. After cooling down the precipitate formed was filtered off, washed with isopropanol (30 ml), acetone (10 ml) and dried giving 3.7 g of the title compound.

후처리

  1. customovernight
  2. customat room temperature
  3. washAfter washing with 50 ml of a 1N hydrochloric acid solution and brine and filtration the organic layer
  4. concentrationwas concentrated
  5. additionAfter addition of hot isopropanol (150 ml) the mixture
  6. filtrationwas filtered while still hot
  7. temperatureAfter cooling down the precipitate
  8. customformed
  9. filtrationwas filtered off
  10. washwashed with isopropanol (30 ml), acetone (10 ml)
  11. customdried

출처 및 근거

ORD 기록
ord-88986c4a8f754e1ba496b1b0d6f87f44
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06054599

반응 노트

불러오는 중…