1,2-Dichloroethane → cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate

HRID 919104ノート

反応式

HRID 919104 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9](CC1CCCCC1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:20]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21]1.[CH2:26](Cl)[CH2:27]Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:27]1[CH2:26][CH2:22][CH2:21][CH2:20][CH2:24]1)[C:10]([O:25][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

生成物 1

HCID 57658394cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate収率 235.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (S)-2-tert-butoxycarbonylamino-3-cyclohexyl-propionic acid (5 g, 19.4 mmol) in DMF (50 mL) at 0° C. was added cyclopentanol (8.8 ml, 97.15 mmol), EDC (4.09 g, 21.37 mmol) and finally DMAP (237 mg, 1.94 mmol). The reaction mixture was warmed to RT and stirred for 18 h. The DMF was removed in vacuo to give a clear oil. This was separated between water and EtOAc. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude extract was purified by column chromatography (25% EtOAC in heptane) to yield the desired product as a clear oil (14.87 g, 55%). 1H NMR (300 MHz, d6-DMSO) δ: 7.09 (1H, d), 5.08 (1H, t), 3.76 (1H, t), 1.50-1.85 (10H, br m), 1.39 (9H, s), 1.00-1.25 (9H, br m).

後処理

  1. customThe DMF was removed in vacuo
  2. customto give a clear oil
  3. customThis was separated between water and EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. extractionThe crude extract
  7. customwas purified by column chromatography (25% EtOAC in heptane)

出典と根拠

ORDレコード
ord-b90927177fba4b299c0faf6446733a84
出典データセット
uspto-grants-2016_03
特許番号
US09273003B2

反応ノート

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