Ethylmorpholine → N-[N-(tert-butoxycarbonyl)-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester

HRID 362146ノート

反応式

HRID 362146 の反応式
[CH2:1]([O:8][C:9](=[O:25])[C@H:10]([CH2:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[NH:11][C:12]([O:14]C(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:38]([O:42][C:43]([NH:45][C@H:46](C(O)=O)[C:47]([CH3:50])([CH3:49])[CH3:48])=[O:44])([CH3:41])([CH3:40])[CH3:39].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N1CCOCC1)C>C(#N)C.ClCCl>[CH2:1]([O:8][C:9](=[O:25])[C@H:10]([CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)[NH:11][C:12](=[O:14])[C@H:46]([C:47]([CH3:50])([CH3:49])[CH3:48])[NH:45][C:43]([O:42][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

9

反応物 6

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acidHCID 54072905N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine benzyl ester

生成物 1

HCID 54225868N-[N-(tert-butoxycarbonyl)-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester収率 61.4%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

1.54 g (4.44 mmol) of N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine benzyl ester and 2.53 g (13.32 mmol) of 4-toluenesulphonic acid hydrate were dissolved in 20 ml of acetonitrile and the solution was left to standat room temperature for 18 hours. The white precipitate formed was filteredoff and added to a mixture of 867 mg (3.75 mmol) of N-(tert-butoxycarbonyl)-3-methyl-L-valine, 557 mg (3.64 mmol) of 1-hydroxybenzotriazole, 793 mg (4.14 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 475 mg (4.13 mmol) of N-ethylmorpholine in 25 ml of dichloromethane and stirred at room temperature for 18 hours. The solution was extracted with 2M hydrochloric acid and saturated sodium bicarbonate solution and then driedover anhydrous magnesium sulphate. Evaporation and chromatography on silicagel using ethyl acetate/petrol (1:3) for the elution gave 1.06 g of N-[N-(tert-butoxycarbonyl)-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester as an off-white foam; MS: m/e 461 [M+H].

後処理

  1. waitthe solution was left
  2. customThe white precipitate formed
  3. extractionThe solution was extracted with 2M hydrochloric acid and saturated sodium bicarbonate solution
  4. customEvaporation and chromatography on silicagel
  5. washfor the elution

出典と根拠

ORDレコード
ord-63b511aa2dd741a7bdb1a86adc9a17b7
出典データセット
uspto-grants-1999_02
特許番号
US05866684

反応ノート

読み込み中…