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

HRID 2246599ノート

反応式

HRID 2246599 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.C(N(CC)CC)C.[CH3:53][S:54](Cl)(=[O:56])=[O:55]>ClCCl>[C:24]([NH:23][C@@H:20]1[CH2:21][CH2:22][C@H:17]([N:14]2[CH2:15][CH2:16][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:13]2=[O:38])[C@H:18]([NH:28][S:54]([CH3:53])(=[O:56])=[O:55])[CH2:19]1)([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866181402-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate

生成物 1

HCID 86618161benzyl (S)-1-((1S,2R,4R)-4-(tert-butylamino)-2-(methylsulfonamido)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A sample of 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate and its 5S diastereomer (100 mg, 0.183 mmol; see Example 11, Step 4) was dissolved in dichloromethane (2 ml) prior to the addition of trifluoroacetic acid (2.54 ml, 32.9 mmol). After 30 min, the solution was concentrated in vacuo. The residue was dissolved in dichloromethane (3 ml) prior to the addition of triethylamine (0.100 ml, 0.720 mmol) and methanesulfonyl chloride (0.018 ml, 0.234 mmol). After 2 h, this was washed with sat NaHCO3 solution and the organic layer was dried (Na2SO4), filtered and concentrated to afford benzyl (S)-1-((1S,2R,4R)-4-(tert-butylamino)-2-(methylsulfonamido)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate as a mixture with its 4S diastereomer (66 mg, 0.137 mmol, 76% yield). LC/MS found [M+H]+=481.22.

後処理

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (3 ml)
  3. waitAfter 2 h
  4. washthis was washed with sat NaHCO3 solution
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2186736fbb664688bb2696d8775e1028
出典データセット
uspto-grants-2010_03
特許番号
US07687508B2

反応ノート

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