Di-tert-butyl dicarbonate → HCID 10331393、化合物

HRID 520352ノート

反応式

HRID 520352 の反応式
[N:1]([C@H:4]1[C:8]([CH3:10])([CH3:9])[CH2:7][O:6][C:5]1=[O:11])=[N+]=[N-].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>CO.C(Cl)Cl.CCOC(C)=O.[Pd]>[CH3:9][C:8]1([CH3:10])[CH2:7][O:6][C:5](=[O:11])[C@H:4]1[NH:1][C:13](=[O:12])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]

参加物

7

反応物 2

HCID 90495Di-tert-butyl dicarbonateHCID 10057735(S)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

生成物 1

HCID 10331393HCID 10331393、化合物

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)-3-azido-4,4-dimethyldihydrofuran-2(3H)-one (5.52 g) in MeOH 910 mL) was added 10% Pd/C (0.379 g, 0.356 mmol) under N2. The reaction mixture was stirred under H2 at rt for 16 hrs. The reaction was filtered through diatomaceous earth (Celite®), washed with EtOAc and the filtrate was concentrated to yield a clear oil. To the above oil in DCM (10 mL) was added BOC2O (9.09 mL) and TEA (13.88 mL). The reaction mixture was stirred at rt for 16 hrs. The reaction mixture was diluted with EtOAc, washed with sat. NaHCO3, citric acid, water, sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield an oil. The crude product was purified by silica gel chromatography (0-100% EtOAc in hexane) to yield (S)-tert-butyl 4,4-dimethyl-2-oxotetrahydrofuran-3-ylcarbamate (3.8 g) as a white solid. LC/MS (Cond. N-1): [M+Na]+ 252.06, RT=2.75 min. 1H NMR (400 MHz, CHLOROFORM-d) ppm 4.81-4.95 (1H, m), 4.38 (1H, d, J=7.78 Hz), 3.97-4.07 (2H, m), 1.47 (9H, s), 1.25 (3H, s), 1.01 (3H, s).

後処理

  1. filtrationThe reaction was filtered through diatomaceous earth (Celite®)
  2. washwashed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customto yield a clear oil
  5. stirringThe reaction mixture was stirred at rt for 16 hrs
  6. washwashed with sat. NaHCO3, citric acid, water, sat. NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield an oil
  11. customThe crude product was purified by silica gel chromatography (0-100% EtOAc in hexane)

出典と根拠

ORDレコード
ord-2500128def064324a78f9ab3b52dfdd6
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

反応ノート

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