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

HRID 919104노트

반응식

HRID 919104 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b90927177fba4b299c0faf6446733a84
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273003B2

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