Hydrochloric Acid → 669713-61-5

HRID 1820195Notes

Reaction equation

HRID 1820195 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14]C)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53847325HCID 53847325, compound

Product 1

HCID 4712650669713-61-5Yield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((tert-butoxycarbonyl)aminomethyl)benzoate (600 mg, 1.99 mmol, 1 eq) was dissolved in 5 mL of THF at 25° C. 1 N NaOH (5.96 mL, 5.96 mmol, 3 eq) was added and the reaction stirred for 20 hours. After this time, 1.0 N HCl (5.86 mL) was added and the product was extracted 3 times with chloroform. The organic extracts were combined, dried over sodium sulfate and stripped to give 2-((tert-butoxycarbonyl)aminomethyl)benzoic acid (560 mg, 98% yield). MS (M+H—BOC)+ found: 152.3.

Workup

  1. extractionthe product was extracted 3 times with chloroform
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-20ff5bd5535d454cb8a7cc47a3dbef35
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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