Dicyclohexylcarbodiimide → HCID 54135793, compound

HRID 892390Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]([O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:6])=[O:4].[CH2:17]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[N:40][C:39]([C:42](O)=[O:43])=[CH:38][N:37]=2)=[CH:32][CH:31]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C@H:5]([O:7][C:8]([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:42]([C:39]2[N:40]=[CH:41][C:36]([C:33]3[CH:34]=[CH:35][C:30]([O:29][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][CH:32]=3)=[N:37][CH:38]=2)=[O:43])=[CH:13][CH:14]=1)=[O:16])[CH3:6])=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

In a 50 ml round flask were charged 86.3 mg (0.39 mmol) of (R)-4-hydroxybenzoic acid 1-(methoxycarbonyl)ethyl ester obtained in Example 1-2), 134.6 mg (0.35 mmol) of 2-(4-dodecyloxyphenyl)-5-pyrazinecarboxylic acid, 4.3 mg (0.035 mmol) of N,N-dimethyl-4-aminopyridine, and 5 ml of methylene chloride, followed by stirring at 25° C. To the mixture was added 79.4 mg (0.39 mmol) of DCC to conduct a reaction at 25° C. for 18 hours. After completion of the reaction, the reaction mixture was worked-up in the same manner as in Example 1-3) to obtain 27.6 mg (0.047 mmol) of Compound (11) in a yield of 13% based on 2-(4-dodecyloxyphenyl)-5-pyrazinecarboxylic acid.

Workup

customa reaction at 25° C. for 18 hours
customAfter completion of the reaction

Sources & evidence

ORD record: ord-ed1b9227479545e2923dd8516d4d7076
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05118442

Reaction notes

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