Tetrahydrofuran → HCID 54053874, compound

HRID 1634029Notes

Reaction equation

HRID 1634029 reaction equation
CON(C)[C:4]([CH:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[CH2:28]([O:27][CH2:26][C:4](=[O:5])[CH:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:24]1[CH:25]=[CH:8][CH:7]=[CH:6][CH:4]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 19364683HCID 19364683, compound

Product 1

HCID 54053874HCID 54053874, compound

Conditions

Temperature
-60 °C

Procedure

The mixture was cooled to −60° C. and stirred under nitrogen while a solution comprised of tert-butyl 1-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate (17 g, 52.73 mmol) in anhydrous THF was added via syringe and the mixture was stirred until the reaction was complete. The reaction was quenched slowly with ammonium chloride solution and the mixture was stirred for 15-30 minutes. The mixture was extracted with ethyl acetate (3×7 mL) and the combined extract was dried (Mg2SO4), filtered and concentrated. Product was purified from the residue by flash column chromatography using silica gel 60 to provide tert-butyl 3-benzyloxy-2-oxo-1-phenethylpropylcarbamate (17.15 g, 44.72 mmol). 1H NMR (CDCl3): δ 1.43 (s, 9H), δ 1.74-1.82 (m. 1H), δ 2.14-2.16 (m, 1H), δ 2.60-2.67 (m, 2H), δ 4.13-4.14 (d, 2H), δ 4.49-4.61 (m, 3H), δ 5.14-5.17 (d, 1H), δ 7.1-7.4(m, 10H).

Workup

  1. additionwas added via syringe
  2. stirringthe mixture was stirred until the reaction
  3. customThe reaction was quenched slowly with ammonium chloride solution
  4. stirringthe mixture was stirred for 15-30 minutes
  5. extractionThe mixture was extracted with ethyl acetate (3×7 mL)
  6. extractionthe combined extract
  7. dry with materialwas dried (Mg2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customProduct was purified from the residue by flash column chromatography

Sources & evidence

ORD record
ord-896348c197554a43be01e863d85f35d6
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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