1,2-Dichloroethane → 4-[(S)-4-tert-Butoxycarbonyl-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-naphthalene-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid butyl ester

HRID 1185508ノート

反応式

HRID 1185508 の反応式
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:44])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][CH2:39][C:40]([OH:42])=O)[C:35]3[C:30](=[CH:31][C:32]([CH3:43])=[CH:33][CH:34]=3)[CH:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(Cl)CCl.FC1C(O)=C(F)C(F)=C(F)C=1F.Cl.[CH:62]1([NH:66][C:67]([C@@H:69]2[CH2:73][CH2:72][CH2:71][NH:70]2)=[O:68])[CH2:65][CH2:64][CH2:63]1>C(Cl)Cl.O>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:44])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][CH2:39][C:40]([N:70]3[CH2:71][CH2:72][CH2:73][C@H:69]3[C:67](=[O:68])[NH:66][CH:62]3[CH2:63][CH2:64][CH2:65]3)=[O:42])[C:35]3[C:30](=[CH:31][C:32]([CH3:43])=[CH:33][CH:34]=3)[CH:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 68597555(S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochlorideHCID 685984354-{(S)-4-tert-Butoxycarbonyl-2-[(4-carboxymethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester

生成物 1

HCID 685969714-[(S)-4-tert-Butoxycarbonyl-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-naphthalene-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 670 mg of 4-{(S)-4-tert-Butoxycarbonyl-2-[(4-carboxymethoxy-7-methyl-naphthalene-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester in 10 ml of DCM, 418 mg of EDC, 402 mg of pentafluorophenol was added and the reaction mixture was stirred for 2 h. Then, 329 mg of (S)-Pyrrolidine-2-carboxylic acid cyclobutylamide hydrochloride and 251 mg of NEM in 1.5 ml of DCM was added. After 16 h the reaction mixture was diluted with water. After filtration through a chem Elut® cartridge by eluting with ethyl acetate the solvents were removed under reduced pressure. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 1.5 g

後処理

  1. filtrationAfter filtration through a chem Elut® cartridge
  2. washby eluting with ethyl acetate the solvents
  3. customwere removed under reduced pressure

出典と根拠

ORDレコード
ord-eabb84e43e9a472fa0113e12a71357d4
出典データセット
uspto-grants-2014_03
特許番号
US08669266B2

反応ノート

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