Tetrahydrofuran → HCID 59272924, compound

HRID 1406584Notes

Reaction equation

HRID 1406584 reaction equation
CON(C)[C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].[CH:17]([Mg]Cl)([CH3:19])[CH3:18].[CH3:22][CH2:23][O:24][C:25](C)=[O:26].[CH2:28]1COC[CH2:29]1>>[O:24]1[C:23]2[CH:22]=[C:28]([C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6])[CH:29]=[CH:19][C:17]=2[CH2:18][O:26][CH2:25]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178418918HCID 178418918, compound

Product 1

HCID 59272924HCID 59272924, compound

Procedure

In a separate reaction tube was (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (1 g, 4.31 mmol) suspended in THF (5 mL) and cooled in an ice/acetone bath to below −5° C., isopropylmagnesium chloride, 2M solution in THF (2.5 mL, 5.00 mmol) was slowly added to form an solution. To this solution was added the above freshly prepared grignard reagent. The mixture was allowed to reach room temperature and stirred for 4 hours. The reaction mixture was slowly poured into ice-cold 150 mL 1M HCl, EtOAc (150 mL) was added and the mixture was stirred for a few minutes and transferred to a separation funnel. The organic phase was washed with water and brine, dried over MgSO4, filtered and concentrated. The obtained crude product was further purified by flash chromatography using an prepacked 70 g silica column with gradient of 10% TBME to 40% TBME in Heptane as eluent. The subtitle compound was obtained as a colourless solid. Yield 790 mg (59%)

Workup

  1. customIn a separate reaction tube
  2. temperaturecooled in an ice/acetone bath to below −5° C.
  3. customto form an solution
  4. customto reach room temperature
  5. additionwas added
  6. stirringthe mixture was stirred for a few minutes
  7. customtransferred to a separation funnel
  8. washThe organic phase was washed with water and brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe obtained crude product
  13. customwas further purified by flash chromatography

Sources & evidence

ORD record
ord-1df307bda3ee4f47b54d9485422886a5
Source dataset
uspto-grants-2014_12
Patent number
US08916600B2

Reaction notes

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