Dicyclohexylcarbodiimide → HCID 52264683, compound

HRID 499193Notes

Reaction equation

[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].ON1C2C=CC=CC=2N=N1.[CH3:25][S:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)(=[O:28])=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:2]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:33](=[O:34])[C:32]2[CH:31]=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:37][CH:36]=2)[CH2:13][CH2:14]1)([CH3:1])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 22 °C

Procedure

To an ice-cooled slurry of 4-N-BOC-amino-piperidine (400.8 mg, 2.0 mmol), 1-hydroxybenzotriazole (HOBt, 342.3 mg, 2.53 mmol), and p-(methylsulfonyl)-benzoic acid (445.9 mg, 2.23 mmol) in dichloromethane (6 mL) is added 1,3-dicyclohexylcarbodiimide (DCC, 496.7 mg, 2.40 mmol). The reaction mixture is stirred at 22° C. for 23 hours. The crude product is purified on a silica gel chromatography with ethyl acetate-hexanes to provide a white solid (692.9 mg, 90.6% yield, ES+(m/z) 383.1 [M+H]).

Workup

customThe crude product is purified on a silica gel chromatography with ethyl acetate-hexanes
customto provide a white solid (692.9 mg, 90.6% yield, ES+(m/z) 383.1 [M+H])

Sources & evidence

ORD record: ord-4e14db80cf0b49198370a1b587aa4e0a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767674B2

Reaction notes

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