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Lithium hydroxide, monohydrate → 4-{(S)-5-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid

HRID 1481909
ノート
印刷プレビュー

反応式

HRID 1481909 の反応式
C[O:2][C:3](=[O:52])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:18][C@H:17]([NH:19][C:20](=[O:32])[C@@H:21]([N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:24])[CH3:22])[C:16](=[O:33])[N:15]([CH2:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([Br:45])=[CH:42][CH:43]=4)[CH:38]=[CH:37][C:36]=3[O:46][CH3:47])[C:14]3[CH:48]=[CH:49][CH:50]=[CH:51][C:13]2=3)=[O:11])=[CH:6][CH:5]=1.O[Li].O>C1COCC1.CO.O.O>[Br:45][C:41]1[CH:40]=[C:39]2[C:44](=[CH:43][CH:42]=1)[C:35]([CH2:34][N:15]1[C:16](=[O:33])[C@@H:17]([NH:19][C:20](=[O:32])[C@@H:21]([N:23]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH3:24])[CH3:22])[CH2:18][N:12]([C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:52])=[O:2])=[CH:5][CH:6]=3)=[O:11])[C:13]3[CH:51]=[CH:50][CH:49]=[CH:48][C:14]1=3)=[C:36]([O:46][CH3:47])[CH:37]=[CH:38]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 902212384-{(S)-5-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid methyl ester2 回

生成物 1

HCID 902209134-{(S)-5-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid収率 91.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

To a solution of 4-{(S)-5-(6-bromo-2-methoxy-naphthalen-1-ylmethyl)-3-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carbonyl}-benzoic acid methyl ester (Intermediate 19) (4 g, 5.175 mmol) in THF-MeOH-water 1:1:1 (90 mL) were slowly added a solution of LiOH.H2O solution (574 mg, 13.6 m mol) in water. After 4 h the mixture was concentrated, the residue was diluted with water and acidified to pH˜3 with 1 N HCl. The mixture was extracted with ethyl acetate, the extracts were dried over sodium sulfate and evaporated. The residue was triturated with hexane to give the title compound (3.6 g, 91.58%) as an off white solid. LC-MS: 759 (M+H).

後処理

  1. concentrationAfter 4 h the mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried over sodium sulfate
  5. customevaporated
  6. customThe residue was triturated with hexane

出典と根拠

ORDレコード
ord-5501cc82b23e4b0db6bbdfa3b7077300
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409888B2

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