Reaction #1702029

Reaction equation

N-(4-hydroxyphenyl)glycine

Benzyl chloroformate

water

→

2-((benzyloxycarbonyl)(4-hydroxyphenyl)amino)acetic acid

Yield 75.0%

Solvents

N-methylpyrrolidone

Conditions

Workup

1. 1
   workup.STIRRINGstirred at ambient conditions for 18 h
2. 2
   workup.WAITstored at 4° C. for 24 h
3. 3
   OtherThe product was isolated
4. 4
   Otherrecrystallized in warm ethanol
5. 5
   Otherdried in vacuum oven at 40° C. overnight (yield 75%, mp=196-198° C.)

Procedure

N-(4-hydroxyphenyl)glycine (55.0 g, 0.330 mol) was dissolved in 275 mL of N-methylpyrrolidone in a 1 L round-bottomed flask. Benzyl chloroformate (50.1 mL, 0.352 mol) was added with stirring over a 40 min period and then stirred at ambient conditions for 18 h. Deionized water was added until slightly turbid and then stored at 4° C. for 24 h. The product was isolated and recrystallized in warm ethanol, dried in vacuum oven at 40° C. overnight (yield 75%, mp=196-198° C.). 1H-NMR (500 MHz, DMSO-d6) δ 12.80 (s, 1H, COOH), 9.50 (s, 1H, phenol), 7.58-6.95 (m, 7H, aryl), 6.74 (s, 2H, aryl), 5.10 (d, J=21.9, 2H, —CH2-benzyl), 4.22 (d, J=21.7, 2H, N—CH2-).

Source