Trifluoroacetic anhydride → (4S)‐4‐hydroxy‐4‐{6‐[(5R)‐5‐(methoxymethyl)‐2‐oxo‐ 1,3‐oxazolidin‐3‐yl]‐1,3‐benzothiazol‐2‐ yl}butanenitrile

HRID 2259654Notes

Reaction equation

HRID 2259654 reaction equation
[OH:1][C@H:2]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([N:17]3[CH2:21][C@H:20]([CH2:22][O:23][CH3:24])[O:19][C:18]3=[O:25])[CH:14]=[CH:13][C:11]=2[N:12]=1)[CH2:3][CH2:4][C:5](=O)[NH2:6].O1CCOCC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[OH:1][C@H:2]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([N:17]3[CH2:21][C@H:20]([CH2:22][O:23][CH3:24])[O:19][C:18]3=[O:25])[CH:14]=[CH:13][C:11]=2[N:12]=1)[CH2:3][CH2:4][C:5]#[N:6]

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 15342518HCID 15342518, compound

Product 1

HCID 9884647(4S)‐4‐hydroxy‐4‐{6‐[(5R)‐5‐(methoxymethyl)‐2‐oxo‐ 1,3‐oxazolidin‐3‐yl]‐1,3‐benzothiazol‐2‐ yl}butanenitrileYield 84.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.0 g of 3-[2-(1(S)-hydroxy-3-carbamoylpropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone was suspended in a liquid mixture of 20 ml of 1,4-dioxane and 3.6 ml of pyridine. 2.0 ml of trifluoroacetic anhydride was added dropwise thereto under cooling with ice for 20 min. The resulting mixture was stirred at room temperature for 2 h and the reaction liquid was added to a saturated aqueous sodium hydrogencarbonate solution. After extraction with ethyl acetate, the organic layer was washed with dilute hydrochloric acid and then with a saturated aqueous common salt solution, and dried. The solvent was distilled off and the resulting residue was crystallized from acetone/water to give 1.6 g of the titled compound.

Workup

  1. temperatureunder cooling with ice for 20 min
  2. customthe reaction liquid
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with dilute hydrochloric acid
  5. customwith a saturated aqueous common salt solution, and dried
  6. distillationThe solvent was distilled off
  7. customthe resulting residue was crystallized from acetone/water

Sources & evidence

ORD record
ord-e36e6b85220c41af94ff160207363755
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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