Hydrochloric Acid → HCID 131709983, compound

HRID 971552Notes

Reaction equation

HRID 971552 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:19]([NH:21][C@H:22]([C:24]([NH:26][C@H:27]([C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])[C@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH3:23])=[O:20])[C@@H:12]([CH3:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].Cl>CN(C)C=O.[Pd]>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:19]([NH:21][C@H:22]([C:24]([NH:26][C@H:27]([C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])[C@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH3:23])=[O:20])[C@@H:12]([CH3:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131711568HCID 131711568, compound

Product 1

HCID 131709983HCID 131709983, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

3.40 g of Z-Gln-Thr(tBu)-Ala-Ile-Gly-OH are dissolved in 70 ml of warm dimethylformamide. After cooling to room temperature, 5 ml of 1 N hydrochloric acid and 500 mg of Pd on charcoal (10%) are added and the product hydrogenated. After completion of the hydrogenation the catalyst is filtered off by filtering through 1 g of Norite and the filtrate is concentrated to about 10 ml in a high vacuum at 40° C. This solution is added dropwise to 100 ml of ether and the precipitated material is filtered off and washed with ether. The product is dried in a high vacuum at room temperature and on potentiometric titration with 0.1 N sodium hydroxide solution in 80% methanol proves to have a content of 91%.

Workup

  1. filtrationAfter completion of the hydrogenation the catalyst is filtered off
  2. filtrationby filtering through 1 g of Norite
  3. concentrationthe filtrate is concentrated to about 10 ml in a high vacuum at 40° C
  4. additionThis solution is added dropwise to 100 ml of ether
  5. filtrationthe precipitated material is filtered off
  6. washwashed with ether
  7. dry with materialThe product is dried in a high vacuum at room temperature and on potentiometric titration with 0.1 N sodium hydroxide solution in 80% methanol

Sources & evidence

ORD record
ord-303ff3da092c4af0a7b0732a79d2f4bf
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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