Hydrochloric Acid → (4S,5S)-4-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,3-oxazolidin-2-one

HRID 1028616Notes

Reaction equation

HRID 1028616 reaction equation
O[C@H:2]([C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C@@H:3]([NH:5][C:6](=[O:15])[O:7]CC1C=CC=CC=1)[CH3:4].Cl>[OH-].[K+].CO.C1COCC1>[CH3:4][C@H:3]1[C@@H:2]([C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)[O:7][C:6](=[O:15])[NH:5]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86603433benzyl [(1S,2S)-2-hydroxy-1-methyl-2-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate

Product 1

HCID 66716948(4S,5S)-4-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of benzyl [(1S,2S)-2-hydroxy-1-methyl-2-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate (53.4 mg, 0.174 mmol) in 7.5 N aqueous KOH (1 mL), MeOH, (2 mL) and THF (4 mL) was stirred at room temperature overnight. The reaction mixture was acidified with 3N HCl and extracted with EtOAc (3×20 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford the product. LCMS calc.=199.1; found=199.1 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 6.92 (s, 1H), 6.82 (s, 1H), 5.91 (d, J=8.2 Hz, 1H), 4.39-4.35 (m, 1H), 2.44 (s, 3H), 0.95 (d, J=6.4 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto afford the product

Sources & evidence

ORD record
ord-e5b7e0a340254c208d040608c6978131
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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