Dicyclohexylcarbodiimide → HCID 54114549, compound

HRID 962358Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)=[N:28][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH:39]1([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]O)[CH2:43][CH2:42][CH2:41][CH2:40]1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:16]([C:24]1[CH:29]=[N:28][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([O:36][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:35])=[CH:32][CH:31]=2)=[N:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.3 g of N,N'-dicyclohexyl-carbodiimide in 6 ml of dichloromethane is added dropwise at 0° C. within 15 minutes to a solution of 0.201 g of 4-(5-octyl-pyrimidin-2-yl)-benzoic acid, 0.116 g of cyclopentane-hexanol and 0.02 g of 4-dimethylaminopyridine in 10 ml of dichloromethane. The suspension is stirred at 0° C. for a further 1 hour, filtered and concentrated. The residue is chromatographed on 10 g of silica gel with hexane/ethyl acetate 19:1 (v/v). Recrystallization of the product-containing fractions from ethanol gives pure 6-cyclopentyl-hexyl 4-(5-octyl-pyrimidin-2-yl)-benzoate.

Workup

filtrationfiltered
concentrationconcentrated
customThe residue is chromatographed on 10 g of silica gel with hexane/ethyl acetate 19:1 (v/v)
customRecrystallization of the product-containing fractions from ethanol

Sources & evidence

ORD record: ord-1dd8ef94f2dd437fbdacdc1147908fb3
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05759443

Reaction notes

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