Ethanol → (S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate

HRID 451764

反応式

HRID 451764 の反応式
[CH:1]1([CH2:7][C@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([N:11](OC)[CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:23](N)C.CCO.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:1]1([CH2:7][C@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([NH:11][CH2:12][CH3:23])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 702EthanolHCID 6341EthylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10495486(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamide

生成物 1

HCID 59201513(S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate収率 34%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (S)-tert-butyl 3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (1.17 g, 4.3 mmol) and TEA (2.4 mL, 17.2 mmol) in anhydrous DMF was added 2.0 M EtNH2 solution in EtOH (6.5 mL, 13 mmol), followed by HBTU (1.96 g, 5.2 mmol). The resulting solution was stirred at rt for 3 h. The reaction was concentrated under reduced pressure and the residue dissolved in EtOAc (50 mL). The mixture was then washed with 1 M NaOH (4 times), 1 M HCl (3 times), sat. aq. NaHCO3, brine, dried over Na2SO4 and filtered. The concentrated residue gave (S)-tert-butyl 3-cyclohexyl-1-(ethylamino)-1-oxopropan-2-ylcarbamate (444 mg, 34%). MS ESI +ve m/z 299 (M+H).

後処理

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (50 mL)
  3. washThe mixture was then washed with 1 M NaOH (4 times), 1 M HCl (3 times), sat. aq. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-9fd7a120d1f64e0ca54472952a0890d1
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

関連ノート

読み込み中…