Dicyclohexylcarbodiimide → HCID 131715815, compound

HRID 2291657Notes

Reaction equation

[N:1]1([C:24]([CH3:26])=[O:25])[CH2:23][CH2:22][CH2:21][C@H:2]1[C:3]([NH:5][C@H:6]([C:18]([OH:20])=O)[CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:38][CH2:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[N:1]1([C:24]([CH3:26])=[O:25])[CH2:23][CH2:22][CH2:21][C@H:2]1[C:3]([NH:5][C@H:6]([C:18]([NH:38][CH2:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])=[O:20])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

5.6 g of Ac-Pro-Orn(Boc)-OH, 5.0 g of the tosylate of H-Gly-OBzl and 2.0 g of HOBt are dissolved in 50 ml of DMF, cooled to 0° C., and 1.9 ml of NEM and 3.4 g of DCC in 5 ml of DMF are added. The mixture is stirred at 0° C. for one hour, and at room temperature overnight. After the urea has been removed by filtration, the solvent is removed by evaporation in vacuo, and the residue is chromatographed on silica gel (system 4). 6.1 g (yield: 79%) of Ac-Pro-Orn(Boc)-Gly-OBzl remain as an oil. Rf (system 4)=0.75; MS (FAB): 519 (M+1).

Workup

customat room temperature
customovernight
customAfter the urea has been removed by filtration
customthe solvent is removed by evaporation in vacuo
customthe residue is chromatographed on silica gel (system 4)

Sources & evidence

ORD record: ord-99491862ed224db4bb5cfc092d0a6ca6
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04797471

Reaction notes

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