Hydrochloric Acid → HCID 59066423, compound

HRID 1837963Notes

Reaction equation

HRID 1837963 reaction equation
Cl.O=[C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:4]1[CH2:5][C@H:6]1[CH2:10][O:9][CH2:8][N:7]1[C:11](=[O:22])[CH2:12][N:13](C)[C:14](OC(C)(C)C)=O.C(O)(C(F)(F)F)=[O:28]>CCOCC>[CH3:14][NH:13][CH2:12][C:11]([N:7]1[C@@H:6]([CH2:5][C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:3]=2)[CH2:10][O:9][C:8]1=[O:28])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6422Trifluoroacetic acidHCID 131724577HCID 131724577, compound

Product 1

HCID 59066423HCID 59066423, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

HCl gas was bubbled into a solution of N-{2-[(4S)-2-oxo4-benzyl(1,3-oxazolidin-3-yl)]-2-oxoethyl}(tert-butoxy)-N-methylcarboxamide (7.2 g, 21 mmol) in Et2O (150 mL) over 30 min. The resulting white slurry was stirred for 2 h, allowed to warm to room temperature, and stirred for 2 h. A solution of HCl (1M in Et2O, 20 mL, 20 mmol, 3.6 equiv) was added and the reaction mixture was stirred overnight, then treated with TFA (10 mL), and stirred for 2 h. HCl gas was again bubbled into the mixture over 15 min, and the reaction was stirred for 3 h. The resulting mixture was concentrated under reduced pressure and the residue was triturated (100 mL of 50% EtOAc/hexanes). The resulting precipitate was filtered and washed with hexanes to give (4S)-3-[2-(methylamino)acetyl]-4-benzyl-1,3-oxazolidin-2-one (5.69 g, 96%) as a white solid: 1H NMR (CDCl3) δ 2.62 (br s, 3H), 2.91-3.04 (m, 2H), 4.22-4.44 (m, 4H), 4.65-4.73 (m, 1H), 7.22-7.34 (m, 5H), 9.26 (br s, 2H); HPLC ES-MS m/z (rel abundance) 249 (MH+, 100%).

Workup

  1. stirringstirred for 2 h
  2. stirringthe reaction mixture was stirred overnight
  3. stirringstirred for 2 h
  4. customHCl gas was again bubbled into the mixture over 15 min
  5. stirringthe reaction was stirred for 3 h
  6. concentrationThe resulting mixture was concentrated under reduced pressure
  7. customthe residue was triturated (100 mL of 50% EtOAc/hexanes)
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with hexanes

Sources & evidence

ORD record
ord-2536d137bc9043f3b266cf2f79e7532e
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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