Hydrochloric Acid → 8-{[(1,1-dimethylethyl)oxy]carbonyl}-2-{N-[(methyloxy)carbonyl]-L-valyl}-2,8-diazaspiro[4.5]decane-3-carboxylic acid

HRID 535134노트

반응식

HRID 535134 반응식
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([N:12]1[CH:16]([C:17]([O:19]CC)=[O:18])[CH2:15][C:14]2([CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:13]1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O.CO>[CH3:31][C:30]([O:29][C:27]([N:24]1[CH2:23][CH2:22][C:14]2([CH2:13][N:12]([C:10](=[O:11])[C@H:6]([CH:7]([CH3:9])[CH3:8])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:16]([C:17]([OH:19])=[O:18])[CH2:15]2)[CH2:26][CH2:25]1)=[O:28])([CH3:33])[CH3:32]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 583131578-(1,1-dimethylethyl) 3-ethyl 2-{N-[(methyloxy)carbonyl]-L-valyl}-2,8-diazaspiro[4.5]decane-3,8-dicarboxylate

생성물 1

HCID 583130918-{[(1,1-dimethylethyl)oxy]carbonyl}-2-{N-[(methyloxy)carbonyl]-L-valyl}-2,8-diazaspiro[4.5]decane-3-carboxylic acid수율 91%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

To a solution of 8-(1,1-dimethylethyl) 3-ethyl 2-{N-[(methyloxy)carbonyl]-L-valyl}-2,8-diazaspiro[4.5]decane-3,8-dicarboxylate (132) (125 mg, 0.27 mmol) in THF/water/MeOH (1.2 mL/0.6 mL/0.6 mL) was added lithium hydroxide monohydrate (22 mg, 0.53 mmol) and the reaction stirred at room temperature for 1.5 h. The reaction was treated with 1N HCl (0.5 mL) and partitioned between EtOAc and 0.1 N HCl (10 mL each) and the aqueous layer extracted with EtOAc (10 mL). The organic layers were combined and dried (MgSO4) and concentrated in vacuo to afford the title compound as a white solid (107 mg, 91% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.29-12.54 (m, 1H) 7.08-7.44 (m, 1H) 4.47 (t, J=5.4 Hz, 1H) 4.13-4.30 (m, 1H) 3.86-4.13 (m, 3H) 3.45-3.58 (m, 3H) 3.16-3.27 (m, 2H) 2.64 (br. s., 1H) 2.15-2.31 (m, 1H) 1.81-1.95 (m, 1H) 1.43-1.67 (m, 3H) 1.29-1.43 (m, 11H) 0.69-1.03 (m, 6H). LC-MS ESI (M−H)−=440.59.

후처리

  1. custompartitioned between EtOAc and 0.1 N HCl (10 mL each)
  2. extractionthe aqueous layer extracted with EtOAc (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-32465bd417fa4a5faa7b128e8d4a9544
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853416B2

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