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

HRID 479928Notes

Reaction equation

HRID 479928 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f112d2e8dd9d45858582fbdbdc310c05
Source dataset
uspto-grants-2003_11
Patent number
US06649230B1

Reaction notes

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