Sodium hydride → HCID 86636842, compound

HRID 1943177Notes

Reaction equation

HRID 1943177 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:10][C:9](=[O:22])[NH:8][C:7]=2[N:23]=1.[H-].[Na+].[N+](C1C=C(S(O[CH2:39][C@@H:40]2[CH2:42][O:41]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:10][C:9](=[O:22])[N:8]([CH2:39][C@@H:40]3[CH2:42][O:41]3)[C:7]=2[N:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 58001787HCID 58001787, compound

Product 1

HCID 86636842HCID 86636842, compoundYield 130.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenylmethyl 6-(methyloxy)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate (11 g, 35.1 mmol) was dissolved in DMF (300 ml) at room temperature under argon to give a yellow solution. The solution was then cooled with an ice bath and treated with sodium hydride (1.685 g, 42.1 mmol). The solution was allowed to warm to room temperature. After 20 minutes (2S)-2-oxiranylmethyl 3-nitrobenzenesulfonate (9.56 g, 36.9 mmol) was added. After 1 h all the starting material was consumed so the reaction was treated with a saturated solution of sodium bicarbonate (350 ml) and the aqueous layer was extracted with DCM (3×400 ml). The combined organic layers were dried on magnesium sulphate, filtered and evaporated to afford a light brown oil (16.93 g). The product was used as crude in the next step.

Workup

  1. customto give a yellow solution
  2. temperatureThe solution was then cooled with an ice bath
  3. customAfter 1 h all the starting material was consumed so the reaction
  4. additionwas treated with a saturated solution of sodium bicarbonate (350 ml)
  5. extractionthe aqueous layer was extracted with DCM (3×400 ml)
  6. customThe combined organic layers were dried on magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-adb09ab479c449538a5de937f2caac50
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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