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

HRID 899454노트

반응식

HRID 899454 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4da144c3c3c640608beecc7b6cb68d7b
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354942B2

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