HCID 178454156, compound → HCID 178454155, compound

HRID 579898Notes

Reaction equation

HRID 579898 reaction equation
[CH2:1](OC(=O)[C@H](CCC(OCC1C=CC=CC=1)=O)N)[C:2]1[CH:7]=CC=[CH:4][CH:3]=1.[NH2:25][C@H:26]([C@H:31]([CH2:33][C:34](=[O:36])[OH:35])[OH:32])[CH2:27][CH:28]([CH3:30])[CH3:29].[NH2:37][C@H:38]([C:40]([OH:42])=[O:41])[CH3:39].N[C@H]([C@H](CC(=O)O)O)CC(C)C.[NH2:55][C@H:56]([C:63]([OH:65])=[O:64])[CH2:57][C:58]1[N:62]=[CH:61][NH:60][CH:59]=1.[C:66]([O:70][C:71]([NH:73][C@H:74]([C:82]([OH:84])=[O:83])[CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)=[O:72])([CH3:69])([CH3:68])[CH3:67]>[OH-].[OH-].[Pd+2].CO>[NH2:55][C@H:56]([C:63]([OH:65])=[O:64])[CH2:57][C:58]1[N:62]=[CH:61][NH:60][CH:59]=1.[C:66]([O:70][C:71]([NH:73][C@H:74]([C:82]([OH:84])=[O:83])[CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)=[O:72])([CH3:69])([CH3:67])[CH3:68].[NH2:37][CH:38]([CH2:39][CH2:1][CH:2]([CH2:3][CH3:4])[CH3:7])[C:40]([OH:42])=[O:41].[NH2:25][C@H:26]([C@H:31]([CH2:33][C:34](=[O:35])[OH:36])[OH:32])[CH2:27][CH:28]([CH3:30])[CH3:29]

Participants

4

Reactant 1

HCID 178454156HCID 178454156, compound

Product 1

HCID 178454155HCID 178454155, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of [N-(t-butyloxycarbonyl)-phenylalanine]-histidine-statine-alanine-statine-glutamic acid dibenzyl ester (90 mg., 0.077 mmoles), 20% Pd(OH)2/C catalyst(45 mg.) and methanol (10 ml.) was hydrogenated for 2 hours at room temperature and 50 psi H2. The reaction mixture was then filtered to remove the catalyst and the filtrate evaporated to yield a foam (72 mg.). This foam was triturated with ether and dried to yield a purified [N-(t-butyloxycarbonyl)-phenylalanine]-histidine-statine-glutamic acid foam (51 mg., 72% yield, 1H NMR, CDCl3, 1.5 delta, 9H s [BOC]).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customto remove the catalyst
  3. customthe filtrate evaporated
  4. customto yield a foam (72 mg.)
  5. customThis foam was triturated with ether
  6. customdried

Sources & evidence

ORD record
ord-e2c191e9142440228dac2983b3d14946
Source dataset
uspto-grants-1988_06
Patent number
US04749687

Reaction notes

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