Dicyclohexylcarbodiimide → Z-Glu(OBzl)-Val-Thr(But)-OBut

HRID 904951Notes

Reaction equation

HRID 904951 reaction equation
[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:10]([CH3:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:7])[CH:3]([CH3:5])[CH3:4].Cl.[CH:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:32][C:33]([CH2:35][CH2:36][C@H:37]([NH:41][C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[C:38](O)=[O:39])=[O:34])=[CH:27][CH:26]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:41]([C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[C@H:37]([C:38]([NH:1][C@H:2]([C:6]([NH:8][C@H:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:10]([CH3:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:39])[CH2:36][CH2:35][C:33](=[O:34])[O:32][CH2:31][C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 30498605-(Phenylmethyl) hydrogen N-((phenylmethoxy)carbonyl)-L-glutamateHCID 131713270H-Val-Thr(But)-OBut.HCl

Product 1

HCID 12944649Z-Glu(OBzl)-Val-Thr(But)-OBut

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.7 g of H-Val-Thr(But)-OBut.HCl are reacted, in 250 ml of dimethylformamide, with 26.0 g of Z-Glu-(OBzl)-OH and 15 g of DCC in the presence of 9.5 g of HOBt. After stirring for 6 hours the mixture is filtered and the filtrate is evaporated to dryness in vacuo. The residue is taken up in ethyl acetate, the solution is washed as described under (A) and, after drying and evaporating off the solvent, 37.3 g of the title compound are obtained with a melting point of 140°-144° (decomposition). Elementary analysis correct (C, H and N).

Workup

  1. filtrationis filtered
  2. customthe filtrate is evaporated to dryness in vacuo
  3. washthe solution is washed
  4. customafter drying
  5. customevaporating off the solvent, 37.3 g of the title compound
  6. customare obtained with a melting point of 140°-144° (decomposition)

Sources & evidence

ORD record
ord-667fbe6c43d94e98b5d1aa7159601041
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

Loading…