Dicyclohexylcarbodiimide → HCID 178451186, compound

HRID 2412330Notes

Reaction equation

HRID 2412330 reaction equation
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13]([OH:15])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10].[NH2:26][C@H:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13]([NH:26][C@H:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 178512184HCID 178512184, compound

Product 1

HCID 178451186HCID 178451186, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Equimolar quantities of Z-D-Arg(NO2)-OH and H-Phe-OtBu were dissolved in DMF and coupled by adding DCC and HOBt under the conditions described in Example 1(2), DCU was filtered off, and the organic EtOAc layer of the filtrate was then extracted successively with acid, base and water, dried and crystallized from EtOAc-hexane mixture. The peptide subsequently purified with the aid of an SiO2 column has an Rf of 0.52 in To/EtOH (4:1).

Workup

  1. filtrationwas filtered off
  2. extractionthe organic EtOAc layer of the filtrate was then extracted successively with acid, base and water
  3. customdried
  4. customcrystallized from EtOAc-hexane mixture
  5. customThe peptide subsequently purified with the aid of an SiO2 column

Sources & evidence

ORD record
ord-fdb8933f212547b1bc4075a862c17d84
Source dataset
uspto-grants-1985_01
Patent number
US04491579

Reaction notes

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