Trifluoroacetic acid → Benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-aminocyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 554743ノート

反応式

HRID 554743 の反応式
[C:1]([NH:4][C@H:5]1[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C:12]2=[O:27])[CH2:9][CH2:8][C@@H:7]([NH:28]C(=O)OC(C)(C)C)[CH2:6]1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[C:1]([NH:4][C@@H:5]1[CH2:6][C@H:7]([NH2:28])[CH2:8][CH2:9][C@@H:10]1[N:11]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:12]1=[O:27])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86618124tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexylcarbamate

生成物 1

HCID 44185158Benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-aminocyclohexyl)-2-oxopyrrolidin-3-ylcarbamate収率 101.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexylcarbamate (100 g, 0.205 mol) in dichloromethane (400 ml) was added TFA (400 ml) at −20° C. The reaction solution was stirred at room temperature for 2 h. The solvent and most of TFA were removed under reduced pressure, and the residue was diluted with dichloromethane (2 L) and aqueous K2CO3 solution (2 L). The pH was adjusted to 10 with 1N HCl. The aqueous layer was extracted with dichloromethane (3×1 L). The combined organic layer was dried over Na2SO4, and concentrated to give benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-aminocyclohexyl)-2-oxopyrrolidin-3-ylcarbamate as an oil (81 g, 100% yield). This amine was used directly in the next step without further purification.

後処理

  1. customThe solvent and most of TFA were removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane (2 L) and aqueous K2CO3 solution (2 L)
  3. extractionThe aqueous layer was extracted with dichloromethane (3×1 L)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8257c00603e94160ab24f40cba79df90
出典データセット
uspto-grants-2011_11
特許番号
US08049019B2

反応ノート

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