Triethylamine → HCID 10371011, compound

HRID 358316Notes

Reaction equation

HRID 358316 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](O)=[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.Cl.[CH2:52]([NH2:54])[CH3:53].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:52]([NH:54][C:35](=[O:36])[C@@H:34]1[CH2:38][CH2:39][CH2:40][N:33]1[C:31](=[O:32])[C@H:23]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:22][C:20](=[O:21])[CH2:19][NH:18][C:16](=[O:17])[C@@H:14]([CH3:15])[NH:13][C:11](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)[NH2:1])[CH3:53]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 11198Ethylamine hydrochlorideHCID 131713663HCID 131713663, compound

Product 1

HCID 10371011HCID 10371011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.7 g. (1 mmoles) of Z-Tyr-D-Ala-Gly-Phe-Pro-OH (3rd step of Example 5) are dissolved in 2 ml. of dimethyl formamide, then 0.1 g. (1.24 mmoles) of ethylamine hydrochloride, 0.17 ml. (1.24 mmoles) of triethylamine and 0.21 g. (1 mmole) of dicyclohexyl-carbodiimide are added. The reaction mixture is allowed to stand for one day, filtered and diluted with 30 ml. of ethyl acetate. The solution is washed with 0.5N sulphuric acid, water, 5% solution of sodium hydrogen carbonate and water, then dried and evaporated. The residue on evaporation (Rf2 0.80-0.85) is dissolved in 30 ml. of methanol and hydrogenated in the presence of palladium as catalyst. At the end of the reaction the catalyst is filtered off, the solution evaporated, rubbed with ether, filtered, washed with ether and dried. Yield: 0.43 g. (75%) of the named pentapeptide; Rf4 0.34-0.44.

Workup

  1. filtrationfiltered
  2. additiondiluted with 30 ml
  3. washThe solution is washed with 0.5N sulphuric acid, water, 5% solution of sodium hydrogen carbonate and water
  4. customdried
  5. customevaporated
  6. customThe residue on evaporation (Rf2 0.80-0.85)
  7. dissolutionis dissolved in 30 ml
  8. customAt the end of the reaction the catalyst
  9. filtrationis filtered off
  10. customthe solution evaporated
  11. filtrationfiltered
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-fe3518b652c9494288ad6d4e01910fac
Source dataset
uspto-grants-1984_08
Patent number
US04465625

Reaction notes

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