Water → HCID 20451953, compound

HRID 1614847Notes

Reaction equation

HRID 1614847 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].O>CN1CCCC1=O>[CH2:17]([O:16][C:14]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10387Benzyl chloroformateHCID 67149N-(4-Hydroxyphenyl)glycine

Product 1

HCID 20451953HCID 20451953, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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-).

Workup

  1. stirringstirred at ambient conditions for 18 h
  2. waitstored at 4° C. for 24 h
  3. customThe product was isolated
  4. customrecrystallized in warm ethanol
  5. customdried in vacuum oven at 40° C. overnight (yield 75%, mp=196-198° C.)

Sources & evidence

ORD record
ord-881ffdc9cc164be399ef28c962fe846d
Source dataset
uspto-grants-2014_07
Patent number
US08765161B2

Reaction notes

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