Dicyclohexylcarbodiimide → Ac-Orn(Boc)-Pro-Gly-OBzl

HRID 2291652Notes

Reaction equation

HRID 2291652 reaction equation
[NH:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].[NH:20]([C:36]([CH3:38])=[O:37])[C@H:21]([C:33](O)=[O:34])[CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CC(=O)OCC>[NH:20]([C:36]([CH3:38])=[O:37])[C@H:21]([C:33]([N:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4])=[O:34])[CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10869079H-Pro-Gly-OBzlHCID 131715814HCID 131715814, compound

Product 1

HCID 131715813Ac-Orn(Boc)-Pro-Gly-OBzlYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

6.4 g of H-Pro-Gly-OBzl, 4.6 g of Ac-Orn(Boc)-OH, 3.0 ml of NEM and 3.1 g of HOBt are dissolved in 30 ml of EA and then 4.8 g of DCC in 10 ml of EA are added. After the mixture has been stirred at room temperature for 24 hours, it is filtered and the filtrate is evaporated. Chromatography of the residue on silica gel (system 1) results in 4.7 g (yield: 41%) of the desired compound being isolated as a colorless powder. Rf (system 1)=0.3; MS (FAB): 519 (M+1).

Workup

  1. filtrationit is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-fabc3214e2884710ab17cc99d027f0b0
Source dataset
uspto-grants-1989_01
Patent number
US04797471

Reaction notes

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