Lithium Hydroxide → (R)-2-(1-(tert-butoxycarbonyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid

HRID 1615750Notes

Reaction equation

HRID 1615750 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:33])[CH2:6][N:7]1[C:12](=[O:13])[C:11]2([CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]2)[N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][C@H:8]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.CO>[C:23]([O:22][C:20]([N:10]1[C:11]2([CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]2)[C:12](=[O:13])[N:7]([CH2:6][C:5]([OH:33])=[O:4])[C@H:8]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:9]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68154106(R)-tert-butyl 4-(2-methoxy-2-oxoethyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Product 1

HCID 68154418(R)-2-(1-(tert-butoxycarbonyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

24 mg (1.0 mmol) lithium hydroxide in 1 ml of water were added to 0.22 g (0.5 mmol) (R)-tert-butyl 4-(2-methoxy-2-oxoethyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate in 10 ml MeOH. The reaction mixture was stirred overnight at RT and then the MeOH was distilled off. The residue was mixed with water and acidified with an aqueous 4N hydrochloric acid. The aqueous phase was extracted with ethyl acetate. The ethyl acetate phase was dried and evaporated down.

Workup

  1. distillationthe MeOH was distilled off
  2. additionThe residue was mixed with water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase was dried
  5. customevaporated down

Sources & evidence

ORD record
ord-761c3dd546b44a119b9dd6a8c0652b04
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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