Sodium hydride → methyl 2-[(3S)-1-Cbz-3-pyrolidinyl(cyclohexyl)amino]acetate

HRID 1670012ノート

反応式

HRID 1670012 の反応式
[H-].[Na+].[C:3]([N:13]1[CH2:17][CH2:16][C@H:15]([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:14]1)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>C1COCC1>[C:3]([N:13]1[CH2:17][CH2:16][C@H:15]([N:18]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:14]1)([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 67343263HCID 67343263、化合物2 回

生成物 1

HCID 67379348methyl 2-[(3S)-1-Cbz-3-pyrolidinyl(cyclohexyl)amino]acetate収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

NaH (60% in mineral oil, 52.0 mg, 1.30 mmol) was placed in a round-bottom flask, filled with nitrogen, and then THF (10 mL) was added. A solution of (3S)-1-Cbz-3-(cyclohexylamino)pyrrolidine (302 mg, 1.00 mmol) prepared in Intermediate 2 in THF was added dropwise at 0° C., and the reaction mixture was stirred for 30 min until no further gas evolution occurred, followed by slow addition of methyl bromoacetate. After 4 h, the reaction, mixture was quenched with water and extracted with EtOAc. The extracts were dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (EtOAc/Hex=1/2) to give the title compound (227 mg, 90.0%).

後処理

  1. additionfilled with nitrogen
  2. additionwas added dropwise at 0° C.
  3. waitAfter 4 h
  4. customthe reaction, mixture
  5. customwas quenched with water
  6. extractionextracted with EtOAc
  7. dry with materialThe extracts were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by column chomatography (EtOAc/Hex=1/2)

出典と根拠

ORDレコード
ord-10f4142bf1eb43fcb524c8da4d5962f8
出典データセット
uspto-grants-2011_08
特許番号
US07989634B2

反応ノート

読み込み中…