1-Hydroxybenzotriazole → 4-[(S)-2-({5-[(S)-2-((S)-2-Benzyloxycarbonyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-4-tert-butoxycarbonyl-butyryl]-piperazine-1-carboxylic acid ethyl ester

HRID 1970434노트

반응식

HRID 1970434 반응식
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:43])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][C@H:32]([C:34]([OH:36])=O)[CH3:33])[N:28]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH2:64]([O:71][C:72](=[O:78])[C@@H:73]1[CH2:77][CH2:76][CH2:75][NH:74]1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:43])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][C@@H:32]([CH3:33])[C:34]([N:74]3[CH2:75][CH2:76][CH2:77][C@H:73]3[C:72]([O:71][CH2:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[O:78])=[O:36])[N:28]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 668551804-((S)-4-tert-Butoxycarbonyl-2-{[5-((S)-1-carboxy-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

생성물 1

HCID 668554344-[(S)-2-({5-[(S)-2-((S)-2-Benzyloxycarbonyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-4-tert-butoxycarbonyl-butyryl]-piperazine-1-carboxylic acid ethyl ester

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2.000 g 4-((S)-4-tert-Butoxycarbonyl-2-{[5-((S)-1-carboxy-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester in 15 ml DMF were added 0.509 g HOBt, 1.37 ml DIPEA and 0.804 g L-proline benzyl ester hydrochloride at RT. Then 0.637 g EDC was added portionwise and the suspension stirred at RT for 12 h. The reaction mixture was diluted with ethyl acetate and subsequently extracted with aqueous LiCl (4% w/w), aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction. Yield: 2.177 g.

후처리

  1. extractionsubsequently extracted with aqueous LiCl (4% w/w), aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-efbc8e26b1bd4f6698d3b5436ed6e7e7
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426420B2

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