Dicyclohexylcarbodiimide → HCID 178476676, compound

HRID 904950Notes

Reaction equation

HRID 904950 reaction equation
C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH:26]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C@H:27]([C:35]([OH:37])=[O:36])[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[NH:34])[NH2:33].[NH2:48][C@H:49]([C:57]([NH:59][C@H:60]([C:70]([NH:72][C@H:73]([C:77]([NH:79][C@H:80]([C:84]([O:86][CH3:87])=[O:85])[CH:81]([CH3:83])[CH3:82])=[O:78])[CH:74]([CH3:76])[CH3:75])=[O:71])[CH2:61][CH2:62][C:63](=[O:69])[O:64]C(C)(C)C)=[O:58])[CH2:50][CH2:51][CH2:52][NH:53][C:54](=[NH:56])[NH2:55].Cl.Cl>CN(C)C=O>[NH:26]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C@H:27]([C:35]([NH:48][C@H:49]([C:57]([NH:59][C@H:60]([C:70]([NH:72][C@H:73]([C:77]([NH:79][C@H:80]([C:84]([O:86][CH3:87])=[O:85])[CH:81]([CH3:82])[CH3:83])=[O:78])[CH:74]([CH3:75])[CH3:76])=[O:71])[CH2:61][CH2:62][C:63](=[O:64])[OH:69])=[O:58])[CH2:50][CH2:51][CH2:52][NH:53][C:54](=[NH:55])[NH2:56])=[O:37])[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[NH:34])[NH2:33].[CH3:27][C:35]([OH:37])=[O:36]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178501512HCID 178501512, compoundHCID 178512917HCID 178512917, compound

Product 1

HCID 178476676HCID 178476676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.68 g of HOBt and 1.1 g of DCC are added successively to 1.54 g of Z-Arg-OH and 3.44 g of the compound prepared in accordance with (B), in 40 ml of dimethylformamide. After stirring overnight, the mixture is filtered, the filtrate is concentrated in vacuo and the residue is digested with ethyl acetate. The tert.-butyl group is split off analogously to Example 1 with trifluoroacetic acid and the compound is converted into its acetate and purified by chromatography on Sephadex® LH 20. Yield 2.9 g, aminoacid analysis: Glu 1.00, Val 1.89 and Arg 2.01.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe tert.-butyl group is split off analogously to Example 1 with trifluoroacetic acid
  4. custompurified by chromatography on Sephadex® LH 20

Sources & evidence

ORD record
ord-6888308b6a6e4de393ea80229b6c9378
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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