Sodium hydride → Tert-butyl 3-(4-fluorophenyl)-4-(2-methoxy-2-oxoethyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

HRID 1615752Notes

Reaction equation

HRID 1615752 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[C:15]2([CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16]2)[C:14](=[O:22])[NH:13][CH:12]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[C:15]2([CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16]2)[C:14](=[O:22])[N:13]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:12]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 68154245Tert-butyl-3-(4-fluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Product 1

HCID 68154635Tert-butyl 3-(4-fluorophenyl)-4-(2-methoxy-2-oxoethyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 mg (0.66 mmol) sodium hydride were added to 0.23 g (0.6 mmol) tert-butyl-3-(4-fluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate in 5 ml DMF. After 5 min at RT 64 μl (0.91 mmol) methyl bromoacetate were added dropwise and then the reaction mixture was stirred for 1 h at RT. The reaction was poured onto ice water and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated down.

Workup

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

Sources & evidence

ORD record
ord-e266a0d270b343248f3ffa578697ea05
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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