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Lithium hydroxide, monohydrate → 3-((2-Tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoic acid

HRID 899463
ノート
印刷プレビュー

反応式

HRID 899463 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:38])([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([C:24]2([C:29]#[N:30])[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:23]=1)[C:16]([O:18]CC)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:38])([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([C:24]2([C:29]#[N:30])[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:23]=1)[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[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

5

反応物 2

HCID 168937Lithium hydroxide, monohydrate2 回HCID 67319292Ethyl 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoate

生成物 1

HCID 673191833-((2-Tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028
Tetrahydrofuran
溶媒

実験手順

A solution of ethyl 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoate (0.13 g, 0.25 mmol) and LiOH.H2O (31 mg, 0.75 mmol) in 6.5 mL THF and 2.5 mL H2O was stirred at rt overnight. Additional LiOH.H2O (25 mg, 0.60 mmol) was added and the reaction was continued for 64 h. The mixture was concentrated, diluted with H2O, made acidic with 10% citric acid solution and extracted with EtOAc. The combined organic layers were washed with brine. Drying and solvent evaporation gave 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoic acid. 1H NMR (500 MHz, CDCl3) δ 8.09 (app d, J=1.5 Hz, 1H), 8.04 (s, 1H), 7.74 (s, 1H), 7.28-7.20 (m, 3H), 7.17 (m, 2H), 4.62 (s, 3H), 3.58 (bs, 1H), 3.48 (d, J=8.5 Hz, 1H), 3.15 (d, J=12.9 Hz, 1H), 2.95 (d, J=13.2 Hz, 1H), 2.54 (m, 2H), 2.14-1.96 (m, 6H), 1.47 (s, 9H), 1.28 (s, 3H).

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customDrying
  6. customsolvent evaporation

出典と根拠

ORDレコード
ord-2a117f74145442efa7996667c25b9e43
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07354942B2

反応ノート

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