Dicyclohexylcarbodiimide → Z-Thr(tBu)-Pro-NH2

HRID 1076424Notes

Reaction equation

HRID 1076424 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[NH:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:12])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 111306L-ProlinamideHCID 7018812(2S,3R)-2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid

Product 1

HCID 14464395Z-Thr(tBu)-Pro-NH2

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

5.27 g of Z-Thr(tBu)-OH and 1.56 g of H-Pro-NH2 are dissolved in 60 ml of acetonitrile, the solution is cooled to 0°C and 3.11 g of dicyclohexylcarbodiimide are added. After 1 hour at 0°C and 20 hours at room temperature the dicyclohexylurea is filtered off and the filtrate is evaporated and the residue taken up in ethyl acetate. The ethyl acetate solution is washed with dilute citric acid solution, soda solution and water, and is dried with sodium sulphate and evaporated. On thin layer chromatography on silica gel plates the colourless residue shows Rf45 = 0.76; Rf43c = 0.70; Rf52 = 0.62.

Workup

  1. filtration20 hours at room temperature the dicyclohexylurea is filtered off
  2. customthe filtrate is evaporated
  3. washThe ethyl acetate solution is washed with dilute citric acid solution, soda solution and water
  4. dry with materialis dried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-a4a7b8d0ca52452b85caff8635c5242f
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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