Sodium Hydroxide → 2-(1-(Tert-butoxycarbonyl)-3-(4-fluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid

HRID 1615753Notes

Reaction equation

HRID 1615753 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[N:15]([CH2:16][C:17]([O:19]C)=[O:18])[C:14](=[O:21])[C:13]3([CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22]3)[N:12]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:11]2)=[CH:6][CH:5]=1>CO>[C:31]([O:30][C:28]([N:12]1[C:13]2([CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22]2)[C:14](=[O:21])[N:15]([CH2:16][C:17]([OH:19])=[O:18])[CH:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[CH2:11]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68154635Tert-butyl 3-(4-fluorophenyl)-4-(2-methoxy-2-oxoethyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Product 1

HCID 681545962-(1-(Tert-butoxycarbonyl)-3-(4-fluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 ml (2.0 mmol) of a 1N aqueous sodium hydroxide solution were added to 0.29 mg (0.61 mmol) tert-butyl 3-(4-fluorophenyl)-4-(2-methoxy-2-oxoethyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate in 5 ml MeOH. After 1 h at RT MeOH was distilled off and the aqueous solution was acidified with 1N hydrochloric acid. The aqueous phase was extracted with ethyl acetate. The ethyl acetate phase was dried and evaporated down.

Workup

  1. distillationAfter 1 h at RT MeOH was distilled off
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate phase was dried
  4. customevaporated down

Sources & evidence

ORD record
ord-691fccf8d85746ff902c488daf28e7df
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

Loading…