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(S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester → (S)-2-[4-[[3,5-difluoro-4-[(S)-1-propoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid propyl ester

HRID 63751
ノート
印刷プレビュー

反応式

HRID 63751 の反応式
[CH2:1]([O:4][C:5](=[O:38])[C@@H:6]([NH:25][C:26](=[O:37])[C:27]1[C:32]([F:33])=[CH:31][C:30]([C:34]#[N:35])=[CH:29][C:28]=1[F:36])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:2][CH3:3]>C(O)CC>[CH2:1]([O:4][C:5](=[O:38])[C@@H:6]([NH:25][C:26](=[O:37])[C:27]1[C:28]([F:36])=[CH:29][C:30]([CH2:34][NH:35][CH2:34][C:30]2[CH:29]=[C:28]([F:36])[C:27]([C:26](=[O:37])[NH:25][C@H:6]([C:5]([O:4][CH2:1][CH2:2][CH3:3])=[O:38])[CH2:7][C:8]3[CH:9]=[CH:10][C:11]([C:14]4[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=4[CH3:20])=[CH:12][CH:13]=3)=[C:32]([F:33])[CH:31]=2)=[CH:31][C:32]=1[F:33])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:12][CH:13]=1)[CH2:2][CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 86691353(S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

生成物 1

HCID 89720749(S)-2-[4-[[3,5-difluoro-4-[(S)-1-propoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid propyl ester収率 39.2%

試薬・触媒・溶媒 1

HCID 1031
1-Propanol
溶媒

実験手順

To a 100 mL flask containing (S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)phenyl]propionic acid propyl ester (524 mg, 1.0 mmol) dissolved in n-propanol (20 mL) purged with nitrogen was added palladium on carbon (10%, 106 mg). The reaction was sealed, degassed with three exposures to nitrogen and house vacuum, and then exposed to a balloon of hydrogen overnight. The reaction was diluted with EA, degassed again, and exposed to hydrogen overnight. The reaction was filtered through celite, concentrated and purified by HPLC yielding the title compound (204 mg, 19%). ES(+)-LRMS m/e calcd. for C54H57F4N7O10 (M+H)+ 1041, obsd 1041.

後処理

  1. custompurged with nitrogen
  2. additionwas added palladium on carbon (10%, 106 mg)
  3. customThe reaction was sealed
  4. customdegassed with three exposures to nitrogen and house vacuum
  5. customexposed to a balloon of hydrogen overnight
  6. additionThe reaction was diluted with EA
  7. customdegassed again
  8. customexposed to hydrogen overnight
  9. filtrationThe reaction was filtered through celite,
  10. concentrationconcentrated
  11. custompurified by HPLC

出典と根拠

ORDレコード
ord-d101ae79daf44e73a29fe5c00293093e
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447035B2

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