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

HRID 2259652Notes

Reaction equation

HRID 2259652 reaction equation
[OH:1][CH:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH:4]=NO.FC(F)(F)C([C:29]1[NH:30]C=CN=1)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:1][C@H:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][C@H:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][C:29]#[N:30]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5654362,2,2-Trifluoro-1-(1H-imidazol-2-yl)ethanoneHCID 73508098HCID 73508098, 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 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

73 g of the 3-[2-(1-hydroxy-3-hydroxyiminopropyl)benzothiazol-6-yl]-5-methoxymethyl-2 -oxazolidinone obtained in the Example 8 was dissolved in 800 ml of tetrahydrofuran. 90 g of trifluoroacetylimidazole was added dropwise to the solution under cooling with ice and the mixture was stirred at room temperature for 4 h. The reaction liquid was poured into an aqueous sodium hydrogencarbonate solution. After extraction with ethyl acetate followed by washing with an aqueous common salt solution, drying over magnesium sulfate and concentration under reduced pressure, the obtained solid was recrystallized from acetone/water to give 51 g of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. extractionAfter extraction with ethyl acetate
  4. washby washing with an aqueous common salt solution
  5. dry with materialdrying over magnesium sulfate and concentration under reduced pressure
  6. customthe obtained solid was recrystallized from acetone/water

Sources & evidence

ORD record
ord-504c034ea2b04ddcaeb496797fa0a37c
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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