Dicyclohexylcarbodiimide → methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate

HRID 2398855ノート

反応式

HRID 2398855 の反応式
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=O)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])=[CH:5][CH:4]=1.Cl.[NH2:24][C@H:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@H:10]([C:18]([NH:24][C@H:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)=[O:20])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 76956Methyl tyrosinate hydrochlorideHCID 919358N-(4-methoxybenzoyl)-phenylalanine

生成物 1

HCID 53971131methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate収率 74%

試薬・触媒・溶媒 1

HCID 21956068Chloroform tetrahydrofuran溶媒

実験手順

In 500 ml of a mixture of chloroform-tetrahydrofuran (2:1), were dissolved 29.9 g of N-(4-methoxybenzoyl)-phenylalanine, 23.2 g of methyl tyrosinate hydrochloride, 10.1 g of trethylamine and 11.6 g of H-hydroxysuccinimide and the mixture was cooled with ice. To the cold solution was added 20.6 g of N,N'-dicyclohexylcarbodiimide. The mixture was stirred for 2 hours and then allowed to sit at room temperature overnight. The precipitates were removed by filtration and the filtrate was concentrated. The residue was extracted with ethyl acetate. The extract was washed with 2% hydrochloric acid, 4% sodium bicarbonate and water, then dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 35 g of methyl N-(4-methoxybenzoyl)-phenylalanyltyrosinate with a mp. 195°-197° C. in a yield of 74%. Analysis, calculated for C27H28O6N2 : C, 68.05; H, 5.92; N, 5.88; found C, 67.84; H, 5.92; N, 5.57.

後処理

  1. temperaturethe mixture was cooled with ice
  2. waitto sit at room temperature overnight
  3. customThe precipitates were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. extractionThe residue was extracted with ethyl acetate
  6. washThe extract was washed with 2% hydrochloric acid, 4% sodium bicarbonate and water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-37445f9f76314754ab2ca962ba3e0028
出典データセット
uspto-grants-1977_05
特許番号
US04025644

反応ノート

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