Sodium hydride → HCID 10248693, compound

HRID 1602663Notes

Reaction equation

HRID 1602663 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C:14]1[C:15](=[O:21])[NH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:22]([O:26][C:27](=[O:30])[CH2:28]Br)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27](=[O:30])[CH2:28][N:16]1[C:17]([CH3:20])=[CH:18][CH:19]=[C:14]([NH:13][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:12])[C:15]1=[O:21])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 100838403-benzyloxycarbonylamino-6-methyl-2-pyridinone

Product 1

HCID 10248693HCID 10248693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

##STR51## Sodium hydride (5.3 g, 0.22 mol) was added to a stirred slurry of 3-benzyloxycarbonylamino-6-methyl-2-pyridinone (16-2; 53.2 g, 0.20 mol) in THF at 0° C. t-Butylbromoacetate (45 ml, 0.27 mol) was added to the resulting solution and a precipitate rapidly forms. The reaction was warmed to rt over 1 h and after 2 h the solvent was evaporated in vacuo and the residue was partitioned between 1:1 water/brine (200 ml) and 6:1 THF/methylene chloride (700 ml). The organic layer was dried (Na2SO4) and evaporated in vacuo to a solid which was triturated with hexane to give the title compound 16-3 as a crystalline solid:

Workup

  1. additionwas added to the resulting solution
  2. customwas evaporated in vacuo
  3. customthe residue was partitioned between 1:1 water/brine (200 ml) and 6:1 THF/methylene chloride (700 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo to a solid which
  6. customwas triturated with hexane

Sources & evidence

ORD record
ord-244f255bfd0a4aa682c91bf41d2e5bc5
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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