2,4-Dinitrophenol → HCID 178512180, compound

HRID 616484Notes

Reaction equation

HRID 616484 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:38]([NH2:40])=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].[NH:51]([C:66]([O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:67])[C@H:52]([C:63]([OH:65])=O)[CH2:53][CH2:54][CH2:55][NH:56][C:57](=[NH:62])[NH:58][N+:59]([O-:61])=[O:60].[N+](C1C=C([N+]([O-])=O)C=CC=1O)([O-])=O.C1CCC(N=C=NC2CCCCC2)CC1>[Pd].O1CCCC1.CN(C=O)C>[NH:51]([C:66]([O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:67])[C@H:52]([C:63]([NH:1][CH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:38]([NH2:40])=[O:39])[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])=[O:65])[CH2:53][CH2:54][CH2:55][NH:56][C:57](=[NH:62])[NH:58][N+:59]([O-:61])=[O:60]

Participants

8

Reactant 4

HCID 14932,4-DinitrophenolHCID 10868DicyclohexylcarbodiimideHCID 131710601HCID 131710601, compoundHCID 178512185HCID 178512185, compound

Product 1

HCID 178512180HCID 178512180, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml. of DMF was dissolved in 1.0 g. of Z-β-Ala-Phe-Phe-Tyr-NH2, and using Pd-black as a catalyst, catalytic reduction was carried out for 6 hours. The catalyst was filtered off. To the filtrate was added a solution of Z-Arg(NO2)-ODNP in tetrahydrofuran (the dinitrophenyl ester prepared from 0.52 g. of Z-Arg(NO2)-OH and 0.30 g. of 2,4-dinitrophenol in 10 ml. of tetrahydrofuran by the DCC process). The mixture was stirred for 13 hours and the solvent was distilled off. To the residue was added 50 ml. of water and the resulting powder was collected by filtration and dried. Yield 1.01 g.(74.9 %); melting point: 192°-194°; α!D22 -11.1° (c=1.02 %, DMF)

Workup

  1. filtrationThe catalyst was filtered off
  2. additionTo the filtrate was added a solution of Z-Arg(NO2)-ODNP in tetrahydrofuran (the dinitrophenyl ester
  3. customprepared from 0.52 g
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added 50 ml
  6. filtrationof water and the resulting powder was collected by filtration
  7. customdried
  8. customα!D22 -11.1° (c=1.02 %, DMF)

Sources & evidence

ORD record
ord-83986e2ecd8041f884d669e9f56336fc
Source dataset
uspto-grants-1978_02
Patent number
US04073890

Reaction notes

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