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

HRID 1615749Notes

Reaction equation

HRID 1615749 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:9]2([CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10]2)[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][C@@H:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:5]1.Br[CH2:30][C:31]([O:33][CH3:34])=[O:32]>CN(C=O)C>[CH3:34][O:33][C:31](=[O:32])[CH2:30][N:5]1[C:4](=[O:3])[C:9]2([CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10]2)[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][C@H:6]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 68154046(3R)-tert-butyl 5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Product 1

HCID 68154106(R)-tert-butyl 4-(2-methoxy-2-oxoethyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24 mg (0.55 mmol) sodium hydride were added to 0.18 g (0.5 mmol) (3R)-tert-butyl 5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate in 3 ml DMF. After 5 min at RT 54 μl (0.91 mmol) methyl bromoacetate were added 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-0f0d64bfe2e544faba0941bc391dc113
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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