Dicyclohexylcarbodiimide → tert-butyl (3S,5R)-3-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(5-methyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

HRID 1259938Notes

Reaction equation

[CH3:1][C:2]1[NH:6][N:5]=NN=1.[C:7]([O:11][C:12]([N:14]1[CH2:19][C@@H:18]([N:20]([C:25]([C:27]2[N:31]([CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[C:30]3[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=3[N:28]=2)=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17][C@@H:16]([C:42](O)=[O:43])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C1CCC(N=C=NC2CCCCC2)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:37][O:36][CH2:35][CH2:34][CH2:33][CH2:32][N:31]1[C:30]2[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=2[N:28]=[C:27]1[C:25]([N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C@H:18]1[CH2:17][C@@H:16]([C:42]2[O:43][C:2]([CH3:1])=[N:6][N:5]=2)[CH2:15][N:14]([C:12]([O:11][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:13])[CH2:19]1)=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

Methyltetrazole (63 mg) and (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (265 mg) were dissolved in toluene (5 ml), DCC (155 mg) was added and the mixture was stirred at 100° C. for 12 hr. The reaction mixture was diluted with ethyl acetate, filtered and the solvent of the mother liquor was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) was concentrated under reduced pressure to give the object product (100 mg).

Workup

filtrationfiltered
customthe solvent of the mother liquor was evaporated under reduced pressure
washa fraction eluted with ethyl acetate-hexane (1:1-1:0)
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-a465476efa134fab8b3ff82ed92d766d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466282B2

Reaction notes

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