Sodium Hydroxide → HCID 67109676, compound

HRID 455300Notes

Reaction equation

HRID 455300 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67110418HCID 67110418, compound

Product 1

HCID 67109676HCID 67109676, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(2-((tert-butoxycarbonylamino)methyl)-5-fluorophenoxy)pentanoate (Example 16; 1.6 mmol) was dissolved in a mixture of THF (6 ml), methanol (6 ml) and water (6 ml). Sodium hydroxide (5.0 mmol) was added and stirred for 2 h. The organic solvent was removed under vacuum, and the aqueous residue was acidified with 1 N HCl to pH=3. The mixture was extracted with ethyl acetate, and the organic phase was removed under vacuum to afford the title compound (0.55 gr) that was used as such in the next step (Example 5.1).

Workup

  1. customThe organic solvent was removed under vacuum
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic phase was removed under vacuum

Sources & evidence

ORD record
ord-5e9c820093d1493c8415aa2a3280b785
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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