Hydrochloric Acid → 3-({2-[(Tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid

HRID 899454ノート

反応式

HRID 899454 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:20]=[C:21]([N:23]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:24][CH2:25][CH3:26])[CH:22]=1)[C:16]([O:18]C)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1>[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:20]=[C:21]([N:23]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:24][CH2:25][CH3:26])[CH:22]=1)[C:16]([OH:18])=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67318237Methyl 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

生成物 1

HCID 588563373-({2-[(Tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoate (462 mg, 0.842 mmol) in THF (15 mL) was added aq. LiOH (4.21 mL, 4.21 mmol, 1N). After stirring vigorously at rt for 20 h, the reaction mixture was acidified to pH 4 with HCl (4.07 nL, 4.07 mmol, 1N), extracted with dichloromethane, dried over sodium sulfate and concentrated in vacuo to provide 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid as a white foam. 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.96 (s, 1H), 7.61 (s, 1H), 7.30-7.20 (m, 3H), 7.18-7.13 (m, 2H) 4.66-4.57 (m, 3H), 3.68 (t, J=7.2 Hz, 2H), 3.59 (A of AB, br d, J=8.5 Hz, 1H), 3.49 (B of AB, br d, J=8.5 Hz, 1H), 3.15 (A of AB, d, J=13.3 Hz, 1H), 2.93 (B of AB, d, J=13.3 Hz, 1H), 2.91 (s, 3H), 1.57-1.45 (m, 2H), 1.47 (s, 9H), 1.27 (s, 3H), 0.92 (t, J=7.4 Hz, 3H).

後処理

  1. extractionextracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4da144c3c3c640608beecc7b6cb68d7b
出典データセット
uspto-grants-2008_04
特許番号
US07354942B2

反応ノート

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