Dicyclohexylcarbodiimide → HCID 178442784, compound

HRID 2372667Notes

Reaction equation

HRID 2372667 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:31]=[CH:30][C:20]([O:21][CH2:22][C:23]3(O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[F:32][C@@H:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34]([OH:36])=[O:35].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[F:32][C@@H:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34]([O:36][C@H:26]1[CH2:27][CH2:28][C@H:23]([CH2:22][O:21][C:20]2[CH:30]=[CH:31][C:17]([C:14]3[N:13]=[CH:12][C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:16][N:15]=3)=[CH:18][CH:19]=2)[CH2:24][CH2:25]1)=[O:35]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13683897(S)-2-fluorocaproic acidHCID 86745590(p-(5-Decyl-2-pyrimidinyl)phenoxymethyl]cyclohexanol

Product 1

HCID 178442784HCID 178442784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.62 g of trans-4-[(p-(5-decyl-2-pyrimidinyl)phenoxymethyl]cyclohexanol, 0.196 g of (S)-2-fluorocaproic acid, 0.413 g of dicyclohexylcarbodiimide and 0.025 g of 4-(dimethylamino)pydidine were dissolved in 25 ml of methylene chloride and stirred at room temperature for 15 hours. The white suspension was subsequently filtered. The residue obtained after evaporation of the solvent from the filtrate was purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 1:9). Subsequent crystallization from 10 ml of ethyl acetate and 50 ml of hexane gave 0.62 g of trans-4-[(p-(5-decyl-2-pyrimidinyl)phenoxy)methyl]cyclohexyl (S)-2-fluorohexanoate as colourless crystals, m.p. (C-S) 88.5° C., phase transitions (S-SC) 108.8° C., (SC -SA) 128° C., cl.p. (SA -I) 137.7° C.

Workup

  1. filtrationThe white suspension was subsequently filtered
  2. customThe residue obtained
  3. customafter evaporation of the solvent from the filtrate
  4. customwas purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 1:9)
  5. customSubsequent crystallization from 10 ml of ethyl acetate and 50 ml of hexane

Sources & evidence

ORD record
ord-e1b5f1f87795446398a45bfddc4d5934
Source dataset
uspto-grants-1992_03
Patent number
US05100577

Reaction notes

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