HCID 178484731, compound → HCID 178484729, compound

HRID 1154760Notes

Reaction equation

HRID 1154760 reaction equation
[NH:1]([CH2:3][C:4]([NH:6][C@H:7]([C:19]([N:21]([CH2:23][C:24]([NH:26][C@H:27]([C:36]([NH2:38])=[O:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:25])[CH3:22])=[O:20])[CH:8](CC1C=CC=CC=1)[C:9](=[O:11])[OH:10])=[O:5])[CH3:2].C1(C[O:46][C:47]([C@@:49](C(Cl)=O)([CH2:51][CH2:52][CH2:53][NH:54][C:55](=[NH:57])[NH2:56])[NH2:50])=O)C=CC=CC=1>C(O)(=O)C.O.[Pd]>[NH2:50][C@H:49]([C:47]([N:1]([CH2:3][C:4]([NH:6][C@H:7]([C:19]([N:21]([CH2:23][C:24]([NH:26][C@H:27]([C:36]([NH2:38])=[O:37])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=1)=[O:25])[CH3:22])=[O:20])[CH2:8][C:9](=[O:11])[OH:10])=[O:5])[CH3:2])=[O:46])[CH2:51][CH2:52][CH2:53][NH:54][C:55](=[NH:56])[NH2:57]

Participants

5

Reactant 1

HCID 178484731HCID 178484731, compound

Product 1

HCID 178484729HCID 178484729, compoundYield 50.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Alpha-Phenylmethoxycarbonyl-L-Arginyl(HCL)-Sarcosyl-beta-benzyl-L-Aspartyl-Sarcosyl-L-Tyrosine amide (1.0 g) was dissolved in 100 ml of 75% aqueous acetic acid and reduced with 0.5 g of 10% Pd/C at 50 p.s.i. for 15 hours. The catalyst was removed by filtration and the solution lyophilized to give 0.8 g. The material was dissolved in 7 ml water, filtered through a 3μ multipore filter, adjusted to pH 5 with NH4OH(conc.) and chromatographed in an SP-C-25 column (2.5×100 cm) with 0.20 M NH4OAc, pH 5.0, 100 ml/hr, 20 ml/tube. Tubes 71 to 78 were pooled and lyophilized to give 0.35 g of Arg-Sar-Asp-Sar-Tyr-NH2.

Workup

  1. customThe catalyst was removed by filtration
  2. customto give 0.8 g
  3. filtrationfiltered through a 3μ multipore filter
  4. customchromatographed in an SP-C-25 column (2.5×100 cm) with 0.20 M NH4OAc, pH 5.0, 100 ml/hr, 20 ml/tube

Sources & evidence

ORD record
ord-aa1349c65c7e4f4d857a8646fc373c0c
Source dataset
uspto-grants-1981_11
Patent number
US04298523

Reaction notes

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