N-((4-Methylphenyl)sulfonyl)-L-phenylalanine → methyl (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoate

HRID 431332노트

반응식

HRID 431332 반응식
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[N:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:36][C@H:37]([C:45](O)=[O:46])[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C1COCC1.C([O-])([O-])=O.[K+].[K+].Cl>[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:36][C@H:37]([C:45]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C@H:4]([N:5]([S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:16][CH:17]([CH3:18])[CH3:19])[C:3]([O:2][CH3:1])=[O:25])=[O:46])[CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

참가 물질

5

반응물 2

HCID 99327N-((4-Methylphenyl)sulfonyl)-L-phenylalanineHCID 22975548Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine methyl ester

생성물 1

HCID 508591methyl (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoate수율 77%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 86626146potassium carbonate THF용매

실험 절차

To a stirred solution of Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine methyl ester (369 mg, 1 mmol, example 65, step C) in THF/K2CO3(1M) (3 mL/3 mL) was added Nα-(4-methylbenzenesulfonyl)-L-phenylalanine N-hydroxysuccinimmide ester (500 mg, 1.2 mmol). The reaction mixture was stirred overnight, then diluted with 1N HCl and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. The crude was purified by flash chromatography using hexane/EtOAc as eluent to afford the desired product (77% yield).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude was purified by flash chromatography

출처 및 근거

ORD 기록
ord-37e2149c61e044ad96134a1cf2122458
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06656965B2

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