Ethyl Acetate → (S)-[(4-Methoxyphenyl)-2-oxo-1-phenylethyl]carbamic Acid Benzyl Ester

HRID 18835Notes

Reaction equation

HRID 18835 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C@H:11]([C:18](=[O:23])N(OC)C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][CH:28]=1.CCOC(C)=O>C1COCC1>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C@@H:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]([C:30]1[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1)=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 59655336(S)-[(N-Methoxy-N-methylcarbamoyl)phenylmethyl]carbamic Acid Benzyl EsterHCID 178491912HCID 178491912, compound

Product 1

HCID 59655493(S)-[(4-Methoxyphenyl)-2-oxo-1-phenylethyl]carbamic Acid Benzyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of the amide 482 (328 mg, 1.0 mmol) in THF (20 mL) is added 0.5M 4-methoxyphenylmagnesium bromide in THF (8.0 mL, 4.0 mmol), and the mixture is allowed to come to rt and stirred at this temperature for 3 h. The reaction mixture is poured into a mixture of ammonium chloride/ice followed by the addition of EtOAc. The organic layer is separated, washed with brine, dried (MgSO4), and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel; elution with heptane:EtOAc (85:15) gives 2.12 g of the product 483. 1H NMR (CDCl3) δ 7.95 (d, 2 H), 7.45-7.20 (m, 10 H), 6.88 (d, 2 H), 6.50-6.20 (m, 2 H), 5.25-5.00 (m, 2 H), 3.81 (s, 3 H)

Workup

  1. customto come to rt
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. customthe residue purified by chromatography on silica gel
  8. washelution with heptane:EtOAc (85:15)

Sources & evidence

ORD record
ord-704b4e45f9174cf5888660d80683aad2
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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