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

HRID 1615767Notes

Reaction equation

HRID 1615767 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:5]=[C:6]([C@H:11]2[N:16]([CH2:17][C:18]([O:20]C)=[O:19])[C:15](=[O:22])[C:14]3([CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23]3)[N:13]([CH3:29])[CH2:12]2)[CH:7]=[C:8]([F:10])[CH:9]=1>C1COCC1.O>[F:10][C:8]1[CH:7]=[C:6]([C@H:11]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15](=[O:22])[C:14]3([CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23]3)[N:13]([CH3:29])[CH2:12]2)[CH:5]=[C:4]([F:3])[CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68154310(R)-methyl 2-(3-(3,5-difluorophenyl)-1-methyl-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)acetate

Product 1

HCID 68763645(R)-2-(3-(3,5-difluorophenyl)-1-methyl-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)-ethanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.2 mg (0.30 mmol) lithium hydroxide were added to 75 mg (0.20 mmol) (R)-methyl 2-(3-(3,5-difluorophenyl)-1-methyl-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)acetate in 5 ml THF and 1 ml of water. The reaction mixture was stirred for 2 h at RT and then MeOH was distilled off. The residue was made neutral with a 0.1M hydrochloric acid solution and evaporated to dryness.

Workup

  1. distillationMeOH was distilled off
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-7cd91da4bea6492a9f783f5ca0b98ddf
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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