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Hydrochloric Acid → 1-{N-[(methyloxy)carbonyl]-L-valyl}-8-oxa-1-azaspiro[4.5]decane-2-carboxylic acid

HRID 1748885
ノート
印刷プレビュー

反応式

HRID 1748885 の反応式
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([N:12]1[C:16]2([CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:15][CH2:14][CH:13]1[C:22]([O:24]CC)=[O:23])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O.CO>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([N:12]1[C:16]2([CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH2:15][CH2:14][CH:13]1[C:22]([OH:24])=[O:23])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]
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 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58313069ethyl 1-{N-[(methyloxy)carbonyl]-L-valyl}-8-oxa-1-azaspiro[4.5]decane-2-carboxylate

生成物 1

HCID 583130871-{N-[(methyloxy)carbonyl]-L-valyl}-8-oxa-1-azaspiro[4.5]decane-2-carboxylic acid収率 77.4%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water
溶媒

実験手順

To a solution of ethyl 1-{N-[(methyloxy)carbonyl]-L-valyl}-8-oxa-1-azaspiro[4.5]decane-2-carboxylate (167) (80 mg, 0.2 mmol) in THF/water/methanol (1.0 mL/0.5 mL/0.5 mL) was added lithium hydroxide monohydrate (13 mg, 0.3 mmol) and the reaction stirred at room temperature for 72 h. The reaction was treated with 1N HCl (0.5 mL) and the reaction partitioned between EtOAc and 0.1 N HCl. The organic layer was separated and dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid (53 mg, 72% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.88 (br. s., 1H) 7.45-7.61 (m, 1H) 4.89-5.03 (m, 1H) 3.70-3.87 (m, 2H) 3.65 (t, J=9.2 Hz, 1H) 3.53 (s, 3H) 3.02 (td, J=12.9, 4.9 Hz, 1H) 2.71-2.90 (m, 1H) 2.22-2.38 (m, 1H) 1.87-2.19 (m, 3H) 1.53-1.73 (m, 1H) 1.32-1.42 (m, 1H) 1.06-1.15 (m, 1H) 0.61-0.98 (m, 8H). LC-MS ESI (M+H)+=342.95.

後処理

  1. customthe reaction partitioned between EtOAc and 0.1 N HCl
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-97328666995046d3a8f38eee79da8e8c
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150587B2

反応ノート

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