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Ammonium formate → N-Hydroxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

HRID 727557
ノート
印刷プレビュー

反応式

HRID 727557 の反応式
C([O:8][NH:9][C:10](=[O:31])[CH2:11][C:12]1([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]1=[O:26])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CCO>[OH:8][NH:9][C:10](=[O:31])[CH2:11][C:12]1([CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]1=[O:26]
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 2

HCID 2723923Ammonium formate2 回HCID 53945587N-Benzyloxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

生成物 1

HCID 17894887N-Hydroxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide収率 31%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of N-benzyloxy-3-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (80 mg, 0.19 mmol), Pd/C (10%, 5 mg), ammonium formate (59 mg, 0.95 mmol) and EtOH (2.5 mL) is stirred at room temperature. After 2 hours, a second portion of ammonium formate (35 mg, 0.56 mmol) is added and the mixture is allowed to stir overnight at room temperature. The mixture is filtered, and the filter cake washed with MeOH (3×15 mL) and CHCl3 (3×15 mL). The filtrate is concentrated, reconstituted in 100 mL of 5% MeOH/CHCl3, dried (MgSO4), filtered and concentrated to an oil. Crystallization from CH2Cl2 /Et2 O/hexane gives 19 mg (31%) of the title compound as a white solid (mp 136°-137° C.).

後処理

  1. stirringto stir overnight at room temperature
  2. filtrationThe mixture is filtered
  3. washthe filter cake washed with MeOH (3×15 mL) and CHCl3 (3×15 mL)
  4. concentrationThe filtrate is concentrated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customCrystallization from CH2Cl2 /Et2 O/hexane

出典と根拠

ORDレコード
ord-aa4ec1c106c94b409e4f80ccbdc85d05
出典データセット
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05712300

反応ノート

読み込み中…

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