Triethylamine → (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate

HRID 451759ノート

反応式

HRID 451759 の反応式
[F:1][C:2]1([CH2:8][C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][OH:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[CH3:20][S:21]([O:11][CH2:10][C@@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[CH2:8][C:2]1([F:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)(=[O:23])=[O:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68713243(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate

生成物 1

HCID 86639447(S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (275 mg, 1.0 mmol, 1.0 equiv) was dissolved in CH2Cl2 and the mixture was cooled to 0° C. To this solution was added methanesulfonyl chloride (230 mg, 2.0 mmol, 2.0 equiv) and triethylamine (304 mg, 3.0 mmol, 3.0 equiv). The mixture was stirred at 0° C. for 0.5 h. After this time LC/MS showed consumption of the starting material. The mixture was transferred to a separatory funnel and 1.0 M aq HCl added. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The crude (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate was used directly in the next step.

後処理

  1. customconsumption of the starting material
  2. customThe mixture was transferred to a separatory funnel
  3. addition1.0 M aq HCl added
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-604bc6bda47947ecb0b6af8f3262fd91
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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