Triethylamine → Nepsilon-Benzyloxycarbonyl-Nalpha-(tert-butoxycarbonyl)-L-lysylglycine ethyl ester

HRID 477709ノート

反応式

HRID 477709 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][C@@H:31]([C:40](O)=[O:41])[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:40](=[O:41])[C@H:31]([CH2:30][CH2:29][CH2:28][CH2:27][NH:26][C:24]([O:23][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:25])[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH3:3]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2724765Boc-Lys(Z)-OH

生成物 1

HCID 13605336Nepsilon-Benzyloxycarbonyl-Nalpha-(tert-butoxycarbonyl)-L-lysylglycine ethyl ester収率 48%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of 0.73 g (5.26 mmol) of glycine ethyl ester hydrochloride and 0.74 mL (5.26 mmol) of triethylamine in 42 mL of chloroform were added successively, at 0° C., 2.0 g (5.26 mmol) of Nε -benzyloxycarbonyl-Nα -(tert-butoxycarbonyl)-L-lysine and 1.09 g (5.26 mmol) of dicyclohexylcarbodiimide. The reaction mixture was stirred overnight at room temperature. The resulting precipitate was removed by filtration and the filtrate was washed successively with 0.5N hydrochloric acid, water, 3% aqueous sodium bicarbonate solution and water, then dried over anhydrous sodium sulfate. Evaporation of the solvent afforded a residue which was triturated with ethyl acetate. Insoluble materials were removed by filtration and the filtrate was evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isopropyl ether to give 1.15 g (48%) of the title compound as colorless crystals. The mother liquor was concentrated under reduced pressure and the residue was crystallized as before to give a second crop of crystals (0.77 g, 32.1%). Total yield 80.1%, melting point 69°-70° C. NMR and IR spectral analyses confirmed the identity of the product, which has the formula: ##STR102##

後処理

  1. customThe resulting precipitate was removed by filtration
  2. washthe filtrate was washed successively with 0.5N hydrochloric acid, water, 3% aqueous sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent
  5. customafforded a residue which
  6. customwas triturated with ethyl acetate
  7. customInsoluble materials were removed by filtration
  8. customthe filtrate was evaporated in vacuo
  9. customThe residue was recrystallized from a mixture of ethyl acetate and isopropyl ether

出典と根拠

ORDレコード
ord-8c697ff2f2d74daf8276a1bc9d8ac770
出典データセット
uspto-grants-1989_12
特許番号
US04888427

反応ノート

読み込み中…