Water → HCID 59176688, compound

HRID 2275816Notes

Reaction equation

HRID 2275816 reaction equation
CON(C)[C:4](=[O:18])[C@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:6].[CH3:20][Mg]Br.C1COCC1.C1(C)C=CC=CC=1.O>C1COCC1>[O:18]=[C:4]([CH3:20])[C@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 10801699HCID 10801699, compoundHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, compound

Product 1

HCID 59176688HCID 59176688, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under argon, 1000 mg of benzyl {(2R)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (Example 149A, 3.8 mmol, 1 equivalent) were dissolved in 19.5 ml of THF and cooled to −78° C. At this temperature, 4 ml of 1.4 M methylmagnesium bromide solution in 1:3 THF/toluene (6 mmol, 1.5 equivalents) were added slowly. The mixture was then stirred at −78° C. for 5 min and at RT for 1 h and then allowed to stand at RT overnight. 0.27 ml of water was then added with ice cooling, and the mixture was then concentrated. The residue was diluted with water and 1 N aqueous hydrochloric acid solution and extracted four times with ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. This gave 888 mg (97% of theory) of the title compound as a colourless oil.

Workup

  1. waitto stand at RT overnight
  2. concentrationthe mixture was then concentrated
  3. additionThe residue was diluted with water and 1 N aqueous hydrochloric acid solution
  4. extractionextracted four times with ethyl acetate
  5. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ef8774c5e57743aaa4fe8fcda062a675
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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