Methanol → L-Tyrosyl-D-alanylglycyl-L-phenylalanyl-L-proline

HRID 358315Notes

Reaction equation

HRID 358315 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([OH:37])=[O:36])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CO>[Pd].CN(C)C=O>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([OH:37])=[O:36])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 131713663HCID 131713663, compound

Product 1

HCID 54502109L-Tyrosyl-D-alanylglycyl-L-phenylalanyl-L-proline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The solution of 2.06 g. (3 mmoles) of Z-Tyr-D-Ala-Gly-Phe-Pro-OH (3rd step of Example 5) in a mixture of 40 ml. of methanol and 10 ml. of dimethyl formamide are hydrogenated in the presence of palladium as catalyst. At the end of the reaction the catalyst is filtered off, washed with a 1:1 mixture of methanol and dimethyl formamide, the combined solutions are evaporated, the residue is rubbed with ether, filtered, washed with ether, dried, redissolved in 4 ml. of ethanol and precipitated with ethyl acetate. The precipitate is filtered, washed with ethyl acetate and dried. Yield: 1.16 g. (70%) of the named pentapeptide; Rf4 0.3-0.4. Aminoacid analysis: Pro=1.02; Gly=1.0; Ala=0.98; Tyr=1.0; Phe=1 (reference basis).

Workup

  1. customAt the end of the reaction the catalyst
  2. filtrationis filtered off
  3. washwashed with a 1:1 mixture of methanol and dimethyl formamide
  4. customthe combined solutions are evaporated
  5. filtrationfiltered
  6. washwashed with ether
  7. customdried
  8. dissolutionredissolved in 4 ml
  9. customof ethanol and precipitated with ethyl acetate
  10. filtrationThe precipitate is filtered
  11. washwashed with ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-d8856570613e401196d9693b2c9576a9
Source dataset
uspto-grants-1984_08
Patent number
US04465625

Reaction notes

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