Ammonium Chloride → HCID 44596871, compound

HRID 553556Notes

Reaction equation

HRID 553556 reaction equation
[C:1]([N:9]1[C@H:13]([CH3:14])[C:12](=[O:15])[O:11][C@H:10]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1.[NH4+].[Cl-]>C1COCC1>[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][C@:13]2([CH3:14])[C:12](=[O:15])[O:11][C@@H:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:9]2[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1650214-Methoxybenzyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 13818180(2S,4R)-3-Benzoyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Product 1

HCID 44596871HCID 44596871, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Compound 2.2 (6.35 g, 0.023 mol) in 50 mL of THF at −78° C. was added over 20 min to a solution of LHMDS in THF (25 mL of 1 M solution in THF). After 10 min, 1.1 eq. of 4-methoxybenzyl bromide (25 mmol, 5 mL) was added in one portion. The mixture was stirred at −78° C. for 3 h and then room temperature overnight. Saturated NH4Cl solution was added, the THF was removed in vacuo, 100 mL of Et2O was added and the phases were separated. The organic layer was washed with 50 mL of NaHCO3 solution and brine. After drying (Na2SO4), filtration and removal of the solvent, the residue was purified by chromatography using Si Gel ISCO column with 9% EtOAc in Hexanes as eluent. Concentration of the product fractions gave 7.4 g (82%) of 2.3 as a white solid. MP 128-129° C.; [α]25D=−260 (c 0.8, MeOH); 1H NMR δ 7.27 (1H, d, J=8 Hz), 7.19-7.14 (2H, m), 7.09-7.05 (4H, m), 6.94 (d, 2H, J=8 Hz), 6.76-6.72 (m, 4H), 5.68 (s, 1H), 3.88 (d, 1H, J=12 Hz), 3.86 (s, 3H), 3.27 (d, 1H, J=12 Hz), 2.14 (s, 3H); C NMR 175.1, 169.4, 159.6, 136.7, 131.5, 130.1, 130.0, 128.8, 128.7, 128.2, 127.2, 126.3, 114.6, 90.7, 65.9, 55.8, 40.5, 24.6; ESI MS 402 (M+1).

Workup

  1. customroom temperature overnight
  2. customthe THF was removed in vacuo, 100 mL of Et2O
  3. additionwas added
  4. customthe phases were separated
  5. washThe organic layer was washed with 50 mL of NaHCO3 solution and brine
  6. customAfter drying
  7. filtration(Na2SO4), filtration and removal of the solvent
  8. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-b3832f035a014ba69c903abd40c6799e
Source dataset
uspto-grants-2011_11
Patent number
US08048895B2

Reaction notes

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