Sodium Hydroxide → HCID 39382716, compound

HRID 1162821Notes

Reaction equation

HRID 1162821 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 (12.4 g, 41.6 mmol) in MeOH (180 mL) was added 5 N aqueous NaOH solution (18.3 mL, 91.6 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, washing 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 combined organic layers were dried (MgSO4) and concentrated in vacuo to afford the title acid as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.26-7.23 (m, 2H), 7.03 (br s, 2H), 4.50 (d, J=13.6 Hz, 2H), 3.96 (br s, 1H), 3.83 (br s, 1H), 1.49 (s, 9H). ES MS (M+1)=284.20

Workup

  1. customThe solvent was removed in vacuo
  2. washwashing 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 combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85974c9ca7254fd09fbda49dfe317577
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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