Trifluoroacetic acid → benzyl (S)-1-((1S,2R,4R)-2-amino-4-(tert-butylamino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 1866107ノート

反応式

HRID 1866107 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:19][C@H:18]2[NH:28]C(=O)OCC[Si](C)(C)C)[C:13]1=[O:38])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:28][C@@H:18]1[CH2:19][C@H:20]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:21][CH2:22][C@@H:17]1[N:14]1[CH2:15][CH2:16][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]1=[O:38]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 866181402-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate

生成物 1

HCID 86618142benzyl (S)-1-((1S,2R,4R)-2-amino-4-(tert-butylamino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Example 1, Alternative Preparation, Step 6: A stirring solution of 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate (100 mg, 0.183 mmol) in dichloromethane (3 mL) was charged with trifluoroacetic acid (2 mL). The reaction was stirred for 2 h at room temperature and concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL) and washed with saturated NaHCO3 (20 mL). The aqueous layer was extracted with dichloromethane (3×30 mL). The dichloromethane layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give benzyl (S)-1-((1S,2R,4R)-2-amino-4-(tert-butylamino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (66 mg, 90%). LC/MS found [M+H]+=403.

後処理

  1. customExample 1, Alternative Preparation, Step 6
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. washwashed with saturated NaHCO3 (20 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (3×30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0d03bd4e2e214320ac56e3d4f32ebcf2
出典データセット
uspto-grants-2009_12
特許番号
US07629351B2

反応ノート

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