4-Pentylbenzoic acid → (E)-2-[4-pentylbenzoyloxy]-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]benzoic acid 11-(2-methylacryloyloxy)undecyl ester

HRID 479928ノート

反応式

HRID 479928 の反応式
[CH3:1][C:2](=[CH2:49])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:48])[C:19]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][O:32][C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([O:43][CH3:44])=[O:42])=[CH:35][C:34]=2[O:45][CH3:46])[CH:22]=[CH:21][C:20]=1[OH:47])=[O:4].[CH2:50]([C:55]1[CH:63]=[CH:62][C:58]([C:59](O)=[O:60])=[CH:57][CH:56]=1)[CH2:51][CH2:52][CH2:53][CH3:54].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:49][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:48])[C:19]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][O:32][C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([O:43][CH3:44])=[O:42])=[CH:35][C:34]=2[O:45][CH3:46])[CH:22]=[CH:21][C:20]=1[O:47][C:59](=[O:60])[C:58]1[CH:62]=[CH:63][C:55]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:56][CH:57]=1)=[O:4]

参加物

6

反応物 3

HCID 334794-Pentylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86759259(E)-2-hydroxy-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]benzoic acid 11-(2-methylacryloyloxy)undecyl ester

生成物 1

HCID 86759258(E)-2-[4-pentylbenzoyloxy]-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]benzoic acid 11-(2-methylacryloyloxy)undecyl ester収率 78.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

1.43 g (2.09 mmol) (E)-2-hydroxy-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]benzoic acid 11-(2-methylacryloyloxy)undecyl ester, 0.42 g (2.20 mmol) 4-pentylbenzoic acid and 64 mg (0.52 mmol) 4-dimethylaminopyridine were dissolved in 30 ml of dichloromethane. A suspension of 0.42 g (2.20 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 3 ml dichloromethane were added dropwise in the course of 15 minutes. After 20 hour at room temperature the reaction mixture was partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 150 g silica gel using cyclohexane:ethyl acetate 4:1 and subsequent crystallisation form 20 ml isopropyl alcohol yielded 1.40 g (78%) (E)-2-[4-pentylbenzoyloxy]-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]benzoic acid 11-(2-methylacryloyloxy)undecyl ester as white crystals.

後処理

  1. additionwere added dropwise in the course of 15 minutes
  2. customAfter 20 hour at room temperature the reaction mixture was partitioned between dichloromethane and water
  3. washthe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-f112d2e8dd9d45858582fbdbdc310c05
出典データセット
uspto-grants-2003_11
特許番号
US06649230B1

反応ノート

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