Dicyclohexylcarbodiimide → HCID 14655931, compound

HRID 1883303Notes

Reaction equation

[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].O[N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[CH2:2][CH2:3][C:4]([O:6][N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of Z-βAla 50 (37.42 g, 0.168 mol) and N-hydroxysuccinimide (19.34 g, 1 equiv) in methylene chloride (700 mL) was stirred at 0° C. and treated with DCC (34.69 g, 1 equiv). The reaction was allowed to warm to rt. After 16 h the DCU was removed by filtration and the filtrate was concentrated in vacuo to give a white foam (53.80 g, 100%). 1H-NMR (CDCl3) δ 2.86 (s and m, 6H), 3.60 (q, 2H), 5.12 (s, 2H), 5.41 (m, 1H), 7.37 (m, 5H). MS (DCl) 321 (MH)+.

Workup

temperatureto warm to rt
customAfter 16 h the DCU was removed by filtration
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-7871f2e67f084e84adc10328479b4ed5
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759509B1

Reaction notes

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