Ethylmorpholine → N-[N-[N-(tert-butoxycarbonyl)-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester

HRID 850891노트

반응식

HRID 850891 반응식
[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[NH:11][C:12](=[O:26])[C@H:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[NH:14]C(OC(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:46]([O:50][C:51]([NH:53][C@H:54]([C:63]([OH:65])=O)[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[CH3:62])=[O:52])([CH3:49])([CH3:48])[CH3:47].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:33])[C@H:10]([CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[NH:11][C:12](=[O:26])[C@H:13]([C:22]([CH3:24])([CH3:23])[CH3:25])[NH:14][C:63](=[O:65])[C@H:54]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[CH3:62])[NH:53][C:51]([O:50][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:52])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 6

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2761468Boc-L-2-MethylphenylalanineHCID 54225868N-[N-(tert-butoxycarbonyl)-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester

생성물 1

HCID 54396325N-[N-[N-(tert-butoxycarbonyl)-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester수율 73.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

993 mg (2.16 mmol) of N-[N-(tert-butoxycarbonyl)-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester and 1.23 g (6.47 mmol) of 4-toluenesulphonic acid hydrate were dissolved in 20 ml of acetonitrile and the solution was stirred at room temperature for 2 hours. The solvent was removed by evaporation and the residue was triturated with diethyl ether and filtered off. The solid obtained was added to a mixture of 602 mg (2.16 mmol) of N-(tert-butoxycarbonyl)-2-methyl-L-phenylalanine, 338 mg (2.21 mmol) of 1-hydroxybenzotriazole, 576 mg (3 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 345 mg (3 mmol) of N-ethylmorpholine in 20 ml of dichloromethane and stirred at room temperature for 18 hours. The solution was extracted with 2M hydrochloric acid and saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulphate and evaporated. Chromatography of the residue on silica gel using ethyl acetate/ petrol (3:7) for the elution gave 990 mg of N-[N-[N-(tert-butoxycarbonyl)-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester as a white solid; MS: m/e 622 [M+H].

후처리

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with diethyl ether
  3. filtrationfiltered off
  4. customThe solid obtained
  5. stirringstirred at room temperature for 18 hours
  6. extractionThe solution was extracted with 2M hydrochloric acid and saturated sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated
  9. washfor the elution

출처 및 근거

ORD 기록
ord-6e24ddd7cc244c8a822f032821b6f745
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06018020

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