2,4-Dinitrophenol → HCID 178512180, compound

HRID 1414684Notes

Reaction equation

HRID 1414684 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 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 byy 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. customof water and the resulting powder was collected byy
  7. filtrationfiltration
  8. customdried

Sources & evidence

ORD record
ord-8bfe03088a34406991c48422369ea48e
Source dataset
uspto-grants-1977_01
Patent number
US04001199

Reaction notes

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