Triethylamine → L-tyrosyl-D-alanyl-glycyl-L-phenylalanyl-L-proline ethylamide

HRID 358316ノート

反応式

HRID 358316 の反応式
[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]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 11198Ethylamine hydrochlorideHCID 131713663HCID 131713663、化合物

生成物 1

HCID 10371011L-tyrosyl-D-alanyl-glycyl-L-phenylalanyl-L-proline ethylamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe3518b652c9494288ad6d4e01910fac
出典データセット
uspto-grants-1984_08
特許番号
US04465625

反応ノート

読み込み中…