Water → HCID 178460470, compound

HRID 2392595Notes

Reaction equation

HRID 2392595 reaction equation
Cl.C(N=C=N[CH2:7][CH2:8][CH2:9][N:10](C)C)C.[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C@H:37]3[CH2:42][CH2:41][C@H:40]([CH2:43][CH2:44][C:45]([OH:47])=[O:46])[CH2:39][CH2:38]3)=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)(=[O:16])[CH:14]=[CH2:15].O[C:49]1[CH:50]=[C:51]([CH:54]=[CH:55][C:56]=1[OH:57])[C:52]#N.[OH2:58]>ClCCl.CN(C)C1C=CN=CC=1>[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]([C@H:37]3[CH2:42][CH2:41][C@H:40]([CH2:43][CH2:44][C:45]([O:47][C:25]4[CH:30]=[C:8]([CH:7]=[CH:27][C:26]=4[O:58][C:45](=[O:46])[CH2:44][CH2:43][C@H:40]4[CH2:39][CH2:38][C@H:37]([C:34]5[CH:33]=[CH:32][C:52]([C:51]6[CH:54]=[CH:55][C:56]([O:57][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:14]=[CH2:15])=[CH:49][CH:50]=6)=[CH:36][CH:35]=5)[CH2:42][CH2:41]4)[C:9]#[N:10])=[O:46])[CH2:39][CH2:38]3)=[CH:35][CH:36]=2)=[CH:27][CH:26]=1)(=[O:16])[CH:14]=[CH2:15]

Participants

7

Reactant 4

HCID 962WaterHCID 870653,4-DihydroxybenzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178460471HCID 178460471, compound

Product 1

HCID 178460470HCID 178460470, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.433 g of N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) in 5 ml of dichloromethane was slowly added dropwise at 20° C. to a solution of 1.00 g of 6-[4'-[trans-4-(2-carboxy-ethyl)-cyclohexyl]-biphenyl-4-yloxy]-hexyl acrylate, 0.127 g of 3,4-dihydroxybenzonitrile and 0.255 g of 4-dimethylamino-pyridine (DMAP) in 30 ml of dichloromethane, the mixture was stirred at room temperature overnight, poured into 50 ml of water and then extracted three times with 25 ml of diethyl ether each time. The combined organic phases were washed twice with 50ml of water each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which were pure according to thin-layer chromatography gave 0.48 g of 3,4-bis-[3-[trans-4-[4'-(6-acryloyloxy-hexyloxy)-biphenyl-4-yl]-cyclohexyl]-propionyloxy]-benzonitrile.

Workup

  1. extractionextracted three times with 25 ml of diethyl ether each time
  2. washThe combined organic phases were washed twice with 50ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationsubsequently concentrated
  6. customChromatographic purification of the residue on silica gel
  7. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which

Sources & evidence

ORD record
ord-3f0870c3fa6c48b5865bd2a54f4c7218
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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