Dimethylformamide → HCID 131723928, compound

HRID 1370235Notes

Reaction equation

HRID 1370235 reaction equation
[CH2:1]1[S:10](=[O:12])(=[O:11])[NH:9][CH2:8][CH:7]2[CH2:13][CH2:14][C:2]1([C:4]2([CH3:6])[CH3:5])[CH3:3].CN(C=O)C.[H-].[Na+].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>>[C:27]([O:26][C:24]([CH2:23][N:9]1[CH2:8][CH:7]2[CH2:13][CH2:14][C:2]([C:4]2([CH3:6])[CH3:5])([CH3:3])[CH2:1][S:10]1(=[O:12])=[O:11])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 129628759HCID 129628759, compound

Product 1

HCID 131723928HCID 131723928, compound

Procedure

Camphorsultam (3 g, 14 mmole) in DMF (25 mol) was mixed with NaH (1.1 equiv.) for 15 minutes, then tert-butyl bromoacetate (2.5 ml) was added and the reaction mixture was stirred overnight. The solvent was evaporated to dryness and the residue was partitioned between aq-citric acid and EtoAc. The organic layer was washed with sat. aq. NaHCO3, and water, dried and evaporated to give the ester. (3.5 g)

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe residue was partitioned between aq-citric acid and EtoAc
  3. washThe organic layer was washed with sat. aq. NaHCO3, and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-776f1b0c76c145d5b3480958ee50473c
Source dataset
uspto-grants-2003_06
Patent number
US06583139B1

Reaction notes

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