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

HRID 454433ノート

反応式

HRID 454433 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2dab22b824b4b7abd14356b301b8275
出典データセット
uspto-grants-2013_07
特許番号
US08492554B2

反応ノート

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