Dicyclohexylcarbodiimide → HCID 178461472, compound
Reaction equation
[CH3:1][C@@H:2]1[CH2:6][C:5](=[O:7])[NH:4][C@@H:3]1[C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:36][C@H:37]([C:44]([N:46]1[CH2:53][CH2:52][CH2:51][C@H:47]1[C:48]([NH2:50])=[O:49])=[O:45])[CH2:38][C:39]1[N:43]=[CH:42][NH:41][CH:40]=1>CN(C=O)C>[CH3:1][C@@H:2]1[CH2:6][C:5](=[O:7])[NH:4][C@@H:3]1[C:8]([NH:36][C@H:37]([C:44]([N:46]1[CH2:53][CH2:52][CH2:51][C@H:47]1[C:48]([NH2:50])=[O:49])=[O:45])[CH2:38][C:39]1[N:43]=[CH:42][NH:41][CH:40]=1)=[O:10]Participants
Conditions
- Temperature
- 0 °C
Procedure
cis-3-Methylpyroglutamic acid [A. B. Mauger, J. Org. Chem. 46, 1032 (1981)] (1.5 g) was dissolved in DMF (30 ml), and HOBT (1.6 g) was added to the solution, followed by addition of DCC (2.81 g) under cooling at 0° C. The mixture was stirred at the same temperature overnight. The above-mentioned DMF solution of L-histidyl-L-prolinamide was added to the mixture, and the mixture was stirred at 5° C. overnight. After the resulting precipitation was filtered off, the filtrate was concentrated to dryness under reduced pressure and the residue was subjected to silica gel column chromatography with chloroform-methanol-ammonia water (40:10:1) as eluent. The eluted fractions were combined and concentrated to dryness to give Nα -(cis-3-methylpyroglutamyl)-L-histidyl-L-prolinamide (2.2 g) as powders.
Workup
- stirringthe mixture was stirred at 5° C. overnight
- customAfter the resulting precipitation
- filtrationwas filtered off
- concentrationthe filtrate was concentrated to dryness under reduced pressure
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-935b0b56ab854060bad3588550e30685
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05151497
Reaction notes
Loading…