Carbon Dioxide → HCID 178500730, compound

HRID 1982327Notes

Reaction equation

HRID 1982327 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:57][CH2:56][CH2:55][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:24]([NH:26][C@H:27]([C@H:32]([CH2:34][C:35]([NH:37][C@H:38]([C:40]([NH:42][C@H:43]([C@H:48]([CH2:50][C:51]([O:53][CH3:54])=[O:52])[OH:49])[CH2:44][CH:45]([CH3:47])[CH3:46])=[O:41])[CH3:39])=[O:36])[OH:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:18][C:19]1[N:23]=[CH:22][NH:21][CH:20]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].C(=O)=O>CO.[Pd]>[NH:1]1[CH2:57][CH2:56][CH2:55][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:24]([NH:26][C@H:27]([C@H:32]([CH2:34][C:35]([NH:37][C@H:38]([C:40]([NH:42][C@H:43]([C@H:48]([CH2:50][C:51]([O:53][CH3:54])=[O:52])[OH:49])[CH2:44][CH:45]([CH3:46])[CH3:47])=[O:41])[CH3:39])=[O:36])[OH:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:18][C:19]1[N:23]=[CH:22][NH:21][CH:20]=1)=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 2

HCID 280Carbon Dioxide2×HCID 178500731HCID 178500731, compound

Product 1

HCID 178500730HCID 178500730, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

125 mg of Z-Pro-Phe-His-Sta-Ala-Sta-OMe (from Example 13), dissolved in 10 ml of 90% strength methanol, are hydrogenated in the presence of 30 mg of palladium-on-carbon catalyst (10% Pd) at 25° under normal pressure with CO2 -absorption (CO2 from the removal of the Z-protecting group) until saturation. The catalyst is then filtered off, the filtrate is concentrated by evaporation and the residue is dried in a high vacuum. H-Pro-Phe-His-Sta-Ala-Sta-OMe (cf. Example 9) is obtained in the form of a colourless foam; Rf (G)=0.12.

Workup

  1. customfrom the removal of the Z-protecting group) until saturation
  2. filtrationThe catalyst is then filtered off
  3. concentrationthe filtrate is concentrated by evaporation
  4. customthe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-2e02b58adaa24b31a8cc6ab1e60c2364
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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