Prednisone → 4-(1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-yloxy)-4-oxobutanoic acid

HRID 1629661

반응식

HRID 1629661 반응식
C[CH2:2][N:3]([CH2:6]C)[CH2:4]C.CN(C)[CH2:10][CH:11](OCCCCCCCC/C=C\C/C=C\CCCCC)[CH2:12][O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C[C@@]12[C@@:84](O)([C:85]([CH2:87][OH:88])=O)[CH2:83][CH2:82][C@H:81]1[C@@H:80]1[CH2:90][CH2:91][C:92]3[C@@:98](C)([C@H:79]1[C:77](=O)[CH2:76]2)[CH:97]=[CH:96][C:94](=O)[CH:93]=3>ClCCl>[CH3:2][N:3]([CH3:6])[CH2:4][CH:12]([O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:10][O:88][CH2:87][CH2:85][CH2:84][CH2:83][CH2:82][CH2:81][CH2:80][CH2:90]/[CH:91]=[CH:92]\[CH2:93]/[CH:94]=[CH:96]\[CH2:97][CH2:98][CH2:79][CH2:77][CH3:76]

참가 물질

6

반응물 4

HCID 5865PrednisoneHCID 8471TriethylamineHCID 2724699PyBOPHCID 583322974-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid

생성물 1

HCID 583322924-(1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-yloxy)-4-oxobutanoic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

NEt3 (100 μL, 0.74 mmol, 1.0 equiv) was added dropwise to a dry dichloromethane solution (10 mL) of 4-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid and the resultant was stirred for 15 minutes under argon at room temperature. PyBOP (0.48 g, 0.93 mmol, 1.25 equiv) was added in one portion and the resultant was stirred for 10 minutes. Prednisone (0.32 g, 0.89 mmol, 1.2 equiv) was added to the mixture and the resultant was stirred at room temperature for 18 hours and then concentrated to provide a thick yellow oil, (90% pure). Purification by flash column chromatography (5-15% MeOH in chloroformand (0-15% MeOH in EtOAc) provided the desired product

후처리

  1. stirringthe resultant was stirred for 10 minutes
  2. stirringthe resultant was stirred at room temperature for 18 hours
  3. concentrationconcentrated
  4. customto provide a thick yellow oil, (90% pure)
  5. customPurification by flash column chromatography (5-15% MeOH in chloroformand (0-15% MeOH in EtOAc)

출처 및 근거

ORD 기록
ord-79652365657c436f874284c7dd76a6cb
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08790691B2

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