Carbon Dioxide → H-Sta-Ala-Sta-OMe

HRID 1982325Notes

Reaction equation

HRID 1982325 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C@H:23]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[OH:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[CH3:14])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(=O)=O>CO.[Pd]>[NH2:1][C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C@H:23]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[OH:24])[CH2:19][CH:20]([CH3:21])[CH3:22])=[O:16])[CH3:14])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 280Carbon Dioxide2×HCID 131714738Z-Sta-Ala-Sta-OMe

Product 1

HCID 13384503H-Sta-Ala-Sta-OMe

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

259 mg of Z-Sta-Ala-Sta-OMe (from stage 13.5) 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 filtered off, the filtrate is concentrated by evaporation and the residue is dried in a high vacuum. H-Sta-Ala-Sta-OMe is obtained in the form of a colourless foam; Rf (chloroform/methanol/ammonia [40:10:1])=0.41; Rf (C)=0.29.

Workup

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

Sources & evidence

ORD record
ord-304fd03139254ae39106ad952ad3d041
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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