Dicyclohexylcarbodiimide → HCID 54147379, compound
Reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][CH2:17][C:18]([N:20]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:19].[CH:57]1[CH:62]=[CH:61][C:60]([CH2:63][O:64][C:65]([NH:67][CH2:68][C:69](O)=[O:70])=[O:66])=[CH:59][CH:58]=1>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:21]([N:20]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:18](=[O:19])[CH2:17][O:16][C:69](=[O:70])[CH2:68][NH:67][C:65]([O:64][CH2:63][C:60]1[CH:59]=[CH:58][CH:57]=[CH:62][CH:61]=1)=[O:66])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]Participants
6
Procedure
A solution of DCC (2.1 g; 10.3 mmol) in CHCl3 (50 mL) was added dropwise to a solution of 2-hydroxy-N,N-dioctadecylacetamide (5 g; 8.6 mmol) and Z-glycine (2 g; 9.5 mmol) in CHCl3 (250 mL). DMAP (0.1 g; 0.9 mmol) was added to the resulting solution. After 1 h the reaction mixture was filtered and the solvent was evaporated. The crude was purified by flash chromatography (n-Hexane/EtOAc=7/3 (v/v)) to give the desired compound (5.6 g; 7.3 mmol). Yield 84%. HPLC: 99% (area %). K.F.: <0.1%. The 13C-NMR, MS and IR spectra were consistent with the structure.
Workup
- filtrationAfter 1 h the reaction mixture was filtered
- customthe solvent was evaporated
- customThe crude was purified by flash chromatography (n-Hexane/EtOAc=7/3 (v/v))
Sources & evidence
- ORD record
- ord-1787c980b3714ab597c09b6148249333
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06652834B2
Reaction notes
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