Diethyl Ether → HCID 66642923, compound

HRID 1868253Notes

Reaction equation

HRID 1868253 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].CCOCC>CO.O>[C:18]([O:17][C:15]([NH:14][CH2:13][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=1[C:3]([OH:22])=[O:2])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 66643062HCID 66643062, compound

Product 1

HCID 66642923HCID 66642923, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino-methyl)-6-nitro-benzoic acid methyl ester (38.96 g, 126 mmol) lithium hydroxide (3.61 g, 151 mmol) in methanol (450 mL) and water (225 mL) was stirred with a mechanical stirrer at room temp overnight. The methanol was evaporated and to the aqueous solution, was added 1 N HCl (200 mL) to form the precipitate. Ether (300 mL) was added, and the mixture was stirred at 0° C. for 2 hours. The suspension was filtered, washed with water (100 mL) and ether (100 mL), and suction dried in hood overnight to give 2-(tert-butoxycarbonylamino-methyl)-6-nitro-benzoic acid as a yellow solid (22.4 g, 60% yield). The product was used in the next step without further purification.

Workup

  1. customThe methanol was evaporated and to the aqueous solution
  2. additionwas added 1 N HCl (200 mL)
  3. customto form the precipitate
  4. stirringthe mixture was stirred at 0° C. for 2 hours
  5. filtrationThe suspension was filtered
  6. washwashed with water (100 mL) and ether (100 mL), and suction
  7. customdried in hood overnight

Sources & evidence

ORD record
ord-72ef25dc927846489b6db4cbdb5f58e9
Source dataset
uspto-grants-2009_12
Patent number
US07635700B2

Reaction notes

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