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Hydrochloric Acid → (2S,4R)-4-benzamido-1-(2-((tert-butoxycarbonyl)amino)acetyl)pyrrolidine-2-carboxylic acid

HRID 1437575
ノート
印刷プレビュー

反応式

HRID 1437575 の反応式
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:4].[OH-].[Na+].Cl>CO>[C:11]([NH:10][C@H:8]1[CH2:7][N:6]([C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]1)(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
参加物反応条件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 14798Sodium HydroxideHCID 25001500Methyl (2S,4R)-4-benzamido-1-((tert-butoxycarbonyl)glycyl)pyrrolidine-2-carboxylate

生成物 1

HCID 16738323(2S,4R)-4-benzamido-1-(2-((tert-butoxycarbonyl)amino)acetyl)pyrrolidine-2-carboxylic acid収率 100.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
-3 °C

実験手順

To a solution of (2S,4R) methyl-4-benzamido-1-(2-(tert-butoxycarbonyl-amino)acetyl)pyrrolidine-2-carboxylate (23.33 g, 0.0575 mol) in methanol (450 mL) was added NaOH (0.2875 mol, 144 mL of 2N aqueous solution) at −1 to 1° C. over 15 min. The mixture was stirred at −5 to −1° C. for 2.5 h. HCl (0.2875 mol, 144 mL of 2N aqueous solution) was added at −3 to 1° C. over 25 min. MeOH was distilled off under vacuum, then 500 mL of EtOAc was added. The aqueous phase was saturated with NaCl and the phases were separated. The aqueous phase was extracted with 2×250 mL EtOAc and the combined EtOAc solution was dried over MgSO4, and concentrated to afford 22.54 g of (2S,4R) 4-benzamido-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid as a white foamy solid (contains 6.6 wt % EtOAc; 94% yield adjusted to residual EtOAc). 1H NMR (CD3OD, δ, ppm): 7.87-7.79 (m, 2 H), 7.58-7.42 (m, 3 H), 4.81-4.7 (m 1 H), 4.69-4.56 (m, 1 H), 4.05-3.72 (m, 3 H), 3.67-3.49 (m, 1 H), 2.64-2.28 (m, 2 H), 1.43 (s, 9 H). MS (m/z, positive ESI) for M+H: 392; for M+Na: 414.

後処理

  1. distillationMeOH was distilled off under vacuum
  2. addition500 mL of EtOAc was added
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with 2×250 mL EtOAc
  5. dry with materialthe combined EtOAc solution was dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-b916b9e41a064027b3f0ed16e74de467
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07622496B2

反応ノート

読み込み中…

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