Sodium hydride → HCID 86636842, compound
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]=1Participants
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 NaHCO3 (350 ml) and the aqueous layer was extracted with DCM (3×400 ml). The combined organic layers were dried over MgSO4, filtered and evaporated to afford a light brown oil (16.93 g). The product was used as crude in the next step.
Workup
- customto give a yellow solution
- temperatureThe solution was then cooled with an ice bath
- customAfter 1 h all the starting material was consumed so the reaction
- additionwas treated with a saturated solution of NaHCO3 (350 ml)
- extractionthe aqueous layer was extracted with DCM (3×400 ml)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-db008027a2584fa9800f52fc1d493a3e
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097628B2
Reaction notes
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