Ammonium formate → HCID 178448353, compound

HRID 2164653Notes

Reaction equation

HRID 2164653 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:30]([N:32]1[CH2:73][CH2:72][CH2:71][C@H:33]1[C:34]([NH:36][C@H:37]([C:49]([NH:51][C@H:52]([C:56]([NH:58][C@H:59]([C:68]([NH2:70])=[O:69])[CH2:60][C:61]1[CH:66]=[CH:65][C:64]([OH:67])=[CH:63][CH:62]=1)=[O:57])[CH:53]([CH3:55])[CH3:54])=[O:50])[CH2:38][C:39](=[O:48])[O:40]CC1C=CC=CC=1)=[O:35])=[O:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:29])[N:8](C(OCC1C=CC=CC=1)=O)C(OCC1C=CC=CC=1)=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C@H:2]([C:30]([N:32]1[CH2:73][CH2:72][CH2:71][C@H:33]1[C:34]([NH:36][C@H:37]([C:49]([NH:51][C@H:52]([C:56]([NH:58][C@H:59]([C:68]([NH2:70])=[O:69])[CH2:60][C:61]1[CH:62]=[CH:63][C:64]([OH:67])=[CH:65][CH:66]=1)=[O:57])[CH:53]([CH3:54])[CH3:55])=[O:50])[CH2:38][C:39](=[O:40])[OH:48])=[O:35])=[O:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:29]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178448350HCID 178448350, compound

Product 1

HCID 178448353HCID 178448353, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Z-Arg(Z,Z)-Pro-Asp(OBzl)-Val-Tyr-NH2 (0.5 g) was hydrogenated with Pd-black (0.5 g) and ammonium formate (0.5 g) in CH3OH (40 ml) overnight. The catalyst was filtered and the filtrate was removed on rotary evaporator. The residue was dissolved in H2O and lyophilized. The crude peptide was then placed on a Sephadex DEAE column (60 cm×2.5 cm) and eluted with 0.01M NH4HCO3 ; pH 7.9. The flow rate was 90 ml/hr and fractions of 10 ml were collected. The peptide was eluted between tubes 17-29, which were pooled and lyophilized to give 290 mg of the title product.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was removed on rotary evaporator
  3. dissolutionThe residue was dissolved in H2O
  4. washeluted with 0.01M NH4HCO3
  5. customThe flow rate was 90 ml/hr and fractions of 10 ml were collected
  6. washThe peptide was eluted between tubes 17-29, which

Sources & evidence

ORD record
ord-cba3e4b5cd8e460ab2a64512fee3e2e1
Source dataset
uspto-grants-1985_03
Patent number
US04505853

Reaction notes

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