Water → N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester

HRID 444423

Reaction equation

HRID 444423 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](Br)[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22].[OH-].[Na+].O>CN(C)C=O>[CH2:20]([O:11][C:10](=[O:12])[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 14798Sodium HydroxideHCID 4189925N-Boc-4-Hydroxyphenyl-DL-glycine

Product 1

HCID 20559123N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl esterYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-tert-butoxycarbonyl-2-(4-hydroxyphenyl) glycine (9.18 g.), phenacyl bromide (6.86 g.) and sodium hydroxide (1.37 g.) in N,N-dimethylformamide (100 ml.) was stirred for 4 hours at ambient temperature. The reaction mixture was poured into water (500 ml.) and extracted three times with every 50 ml. portions of ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and evaporated to dryness under reduced pressure to give an oily N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester (13.19 g.).

Workup

  1. extractionextracted three times with every 50 ml
  2. extractionThe combined extract
  3. washwas washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a0cd57081ebf4a2eb7bdb5177d46e5e6
Source dataset
uspto-grants-1981_04
Patent number
US04264498

Linked notes

Loading…