HCID 131711887, compound → HCID 131711886, compound

HRID 27810Notes

Reaction equation

HRID 27810 reaction equation
[NH2:1][C@H:2]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:35]([C:51]([NH:53][CH2:54][C:55]([NH:57][C@H:58]([C:68]([NH:70][CH2:71][C:72]([NH:74][C@H:75]([C:83]([NH:85][C@H:86]([C:94]([O:96][CH3:97])=[O:95])[CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1)=[O:84])[CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)=[O:73])=[O:69])[CH2:59][O:60]CC1C=CC=CC=1)=[O:56])=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40]C(OCC1C=CC=CC=1)=O)=[O:33])[C@@H:22]([CH3:31])[O:23]CC1C=CC=CC=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.Cl.[H][H]>CC(O)=O.[Pd]>[NH2:1][C@H:2]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:35]([C:51]([NH:53][CH2:54][C:55]([NH:57][C@H:58]([C:68]([NH:70][CH2:71][C:72]([NH:74][C@H:75]([C:83]([NH:85][C@H:86]([C:94]([O:96][CH3:97])=[O:95])[CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1)=[O:84])[CH2:76][C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1)=[O:73])=[O:69])[CH2:59][OH:60])=[O:56])=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])=[O:33])[C@@H:22]([CH3:31])[OH:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 2

HCID 131711887HCID 131711887, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131711886HCID 131711886, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Partially protected octapeptide (IV) (0.10 g) was hydrogenated in 85% AcOH (70 ml) with 10% Pd/C catalyst (0.20 g) over a steady stream of hydrogen for 20 hours. The mixture was filtered, evaporated in vacuo and residue filtered on Sephadex LH20 eluting with water to give the desired octapeptide methyl ester (V) (0.03 g, 46% yield). TLC examination showed 1 spot at Rf 0.2 in 5:2:2 BAW (t-BuOCl/KI-starch stain) and Rf 0.5 in 5:2:3 BAW (Ninhydrin stain). Amino acid analysis:

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo and residue
  3. filtrationfiltered on Sephadex
  4. washLH20 eluting with water

Sources & evidence

ORD record
ord-8268ff933f84494487600bdb000e10d7
Source dataset
uspto-grants-1980_09
Patent number
US04223016

Reaction notes

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