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

HRID 1045267

反応式

HRID 1045267 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 chloroform and (0-15% MeOH in EtOAc) provided the desired product

後処理

  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 chloroform and (0-15% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-d53c6fdfe645492fb31e6183a179c7de
出典データセット
uspto-grants-2013_10
特許番号
US08568772B2

関連ノート

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