Dicyclohexylcarbodiimide → HCID 178512917, compound
Reaction equation
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH2:21]([O:28][C:29]([NH:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:39])[NH2:38])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[NH:31]([C:29]([O:28][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:30])[C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:38])[NH2:39]Participants
Procedure
The amino-component (10 mmol) was dissolved in DMF (70 ml), and 4,59 g (30 mmol monohydrate) HOBT was added. To the solution was diisopropyletylamine (DIPEA) added dropwise, until the pH of the mixture, controlled with wet indicator paper reached 7-8. Next, the N-benzyloxycarbonyl-arginine hydrochloride (5.17 g, 15 mmol) was added and the solution was cooled on ice bath. N,N′-Dicyclohexylcarbodiimide (3.09 g, 15 mmol) was added in small portions during 1 h. and after additional 1 h of stirring, the reaction mixture was left in a cold room overnight (approximately 4° C.). The precipitated DCU was filtered off and washed with a small volume of DMF and the combined filtrates were evaporated under reduced pressure. From the resulting mixture A20 (or its analogues) was isolated using chromatography techniques.
Workup
- additionadded dropwise, until the pH of the mixture
- temperaturethe solution was cooled on ice bath
- filtrationThe precipitated DCU was filtered off
- washwashed with a small volume of DMF
- customthe combined filtrates were evaporated under reduced pressure
- customFrom the resulting mixture A20 (or its analogues) was isolated
Sources & evidence
- ORD record
- ord-5b4f98f3cfaa4de09a479c949880c914
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097582B2
Reaction notes
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