Sodium hydride → HCID 68154152, compound

HRID 1615756Notes

Reaction equation

HRID 1615756 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:10]2[NH:15][C:14](=[O:16])[C:13]3([CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17]3)[N:12]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1.Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:10]2[N:15]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:14](=[O:16])[C:13]3([CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22]3)[N:12]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 68154689HCID 68154689, compound

Product 1

HCID 68154152HCID 68154152, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 mg (0.66 mmol) sodium hydride were added to 0.21 g (0.55 mmol) tert-butyl 3-(3-fluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate in 20 ml DMF. After 20 min at RT 63 μl (0.65 mmol) methyl bromoacetate were added dropwise at 0° C. Then the mixture was stirred for 30 min in the ice bath and then for 5 h at RT. The reaction mixture was poured onto water poured and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated down.

Workup

  1. additionThe reaction mixture was poured onto water
  2. additionpoured
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated down

Sources & evidence

ORD record
ord-1fd4f185b5794d56bd3c98052a260b20
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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