Hydrochloric Acid → HCID 68639140, compound

HRID 1253886Notes

Reaction equation

HRID 1253886 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][N:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15].[OH-].[Li+].Cl>C1COCC1.O>[C:20]([O:19][C:17]([N:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])[CH2:4][C:3]([OH:24])=[O:2])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68629170HCID 68629170, compound

Product 1

HCID 68639140HCID 68639140, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude [tert-butoxycarbonyl-(4-fluoro-2-nitro-benzyl)-amino]-acetic acid methyl ester (5.91 g, 17.2 mmol) in THF (50 mL) was added lithium hydroxide (4.35 g, 103.6 mmol,) dissolved in water (17 mL). The reaction was stirred at r.t. overnight. After completion of the reaction, as confirmed by TLC, the reaction mixture was acidified to pH 4 using 10% HCl and crude compound was extracted with MeOH and CHCl3 (1:9, 3×50 mL). The combined organic layers were dried over Na2SO4. The solvents were removed in vacuo to afford 2-(tert-butoxycarbonyl(4-fluoro-2-nitrobenzyl)amino)-acetic acid (5.11 g, 90%) as brown thick gel, which was used as such without any further purification for the next step.

Workup

  1. customAfter completion of the reaction
  2. extractionwas extracted with MeOH and CHCl3 (1:9, 3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-54ebbef15db7415abc8ec876f7ff4f7d
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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