Dicyclohexylcarbodiimide → HCID 45267115, compound

HRID 1090563Notes

Reaction equation

HRID 1090563 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([OH:23])=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([N:34]1[CH2:33][CH2:32][N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:36][CH2:35]1)=[O:23])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 712438N-benzyloxycarbonyl-l-tyrosine

Product 1

HCID 45267115HCID 45267115, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

21.31 g of N-benzyloxycarbonyltyrosine and 11.79 of N-(tert-butoxycarbonyl)piperazine were dissolved in a mixed solvent of 200 ml of methylene chloride and 100 ml of ethyl acetate, and to the solution was added 14 g of DCC. After stirring at a room temperature for 40 hours, precipitated insoluble matter was filtered off, and the filtrate was concentrated under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (1:1) to obtain 23.9 g of the title compound in a colorless amorphous form

Workup

  1. customprecipitated insoluble matter
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customresulting residue
  5. washeluted with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-70c76fe2a1984ea4a27bcee3b23c48a6
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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