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HCID 72548394、化合物 → (S)-2-[2-(4-{[(2R,3S,4R,5S)-4-(4-chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoyloxy)-acetylamino]-pentanedioic acid

HRID 2206434
ノート
印刷プレビュー

反応式

HRID 2206434 の反応式
C([O:8][C:9](=[O:69])[C@@H:10]([NH:23][C:24](=[O:68])[CH2:25][O:26][C:27](=[O:67])[C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([C@H:37]2[C@H:41]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[C:43]=3[F:49])[C@:40]([C:52]3[CH:57]=[CH:56][C:55]([Cl:58])=[CH:54][C:53]=3[F:59])([C:50]#[N:51])[C@H:39]([CH2:60][C:61]([CH3:64])([CH3:63])[CH3:62])[NH:38]2)=[O:36])=[C:30]([O:65][CH3:66])[CH:29]=1)[CH2:11][CH2:12][C:13]([O:15]CC1C=CC=CC=1)=[O:14])C1C=CC=CC=1>[Pd].C(O)(C)C>[Cl:58][C:55]1[CH:56]=[CH:57][C:52]([C@@:40]2([C:50]#[N:51])[C@H:39]([CH2:60][C:61]([CH3:62])([CH3:64])[CH3:63])[NH:38][C@@H:37]([C:35]([NH:34][C:31]3[CH:32]=[CH:33][C:28]([C:27]([O:26][CH2:25][C:24]([NH:23][C@@H:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:9]([OH:69])=[O:8])=[O:68])=[O:67])=[CH:29][C:30]=3[O:65][CH3:66])=[O:36])[C@@H:41]2[C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[C:43]=2[F:49])=[C:53]([F:59])[CH:54]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 72548394HCID 72548394、化合物

生成物 1

HCID 86704085(S)-2-[2-(4-{[(2R,3S,4R,5S)-4-(4-chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoyloxy)-acetylamino]-pentanedioic acid

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3776Isopropanol溶媒

実験手順

In a 25 mL three-necked flask, (S)-dibenzyl 2-(2-(4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)acetamido)pentanedioate (Example 70, 61 mg, 62.0 μmol) was combined with isopropanol (5 mL) at room temperature. Then palladium on carbon (33.0 mg, 31.0 μmol) was added. The flask was flushed with nitrogen, and then replaced with hydrogen. It was stirred at room temperature under hydrogen balloon. After 30 min, the reaction mix was filtered through a Celite cake to remove the catalyst. The Celite cake was washed thoroughly with isopropanol. The filtrate and washing solutions were combined and concentrated to give a crude product, which was purified with reverse phase high-performance liquid chromatography. The pure fractions were concentrated and lyophilized to give (S)-2-[2-(4-{[(2R,3S,4R,5S)-4-(4-chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoyloxy)-acetylamino]-pentanedioic acid as a white product (20 mg, 33% yield). LCMS (ES+) m/z calcd. for C38H39Cl2F2N4O9 [(M+H)+]: 803. found: 803.

後処理

  1. customThe flask was flushed with nitrogen
  2. additionthe reaction mix
  3. filtrationwas filtered through a Celite cake
  4. customto remove the catalyst
  5. washThe Celite cake was washed thoroughly with isopropanol
  6. washThe filtrate and washing solutions
  7. concentrationconcentrated
  8. customto give a crude product, which
  9. customwas purified with reverse phase high-performance liquid chromatography
  10. concentrationThe pure fractions were concentrated

出典と根拠

ORDレコード
ord-0407842751eb4909b8e950f862114025
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09371280B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート