Sodium Hydroxide → HCID 39382716, compound

HRID 2114824Notes

Reaction equation

HRID 2114824 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:9][C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68430697HCID 68430697, compound

Product 1

HCID 39382716HCID 39382716, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)-N-(4-fluorobenzyl)glycinate (12.37 g, 41.63 mmol) in MeOH (180 mL) was added 5 N aqueous NaOH solution (18.32 mL, 91.58 mmol). The reaction was stirred under inert atmosphere at ambient temperature for 2 h. The solvent was removed in vacuo, and the remaining residue was taken up in water and washed twice with CHCl3. The aqueous layer was cooled to 0° C., acidified to pH 2 with 1 N aqueous HCl solution, and saturated with NaCl. The mixture was extracted with EtOAc three times, and the organic layers were dried (MgSO4) and concentrated in vacuo to afford the acid as a light yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed twice with CHCl3
  3. temperatureThe aqueous layer was cooled to 0° C.
  4. extractionThe mixture was extracted with EtOAc three times
  5. dry with materialthe organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fa570f680cd447eb560b9ec8f35440a
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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