Phenacyl bromide → N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycin phenacyl ester

HRID 444424Notes

Reaction equation

HRID 444424 reaction equation
[CH2:1]([O:10][C:11](=[O:28])[CH:12]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH2:29](Br)[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:10][C:11](=[O:28])[CH:12]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:31])=[CH:25][CH:26]=1)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 20559123N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester

Product 1

HCID 20243679N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycin phenacyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester prepared as above (3.56 g.), phenacyl bromide (1.84 g.) and potassium carbonate (1.28 g.) in an anhydrous acetone (71 ml.) was heated to reflux for 7 hours. The insoluble substances were filtered off and the filtrate was evaporated to dryness under reduced pressure. The residual oil was dissolved in chloroform, washed with water, dried over magnesium sulfate, and evaporated to dryness under reduced pressure. The residue was triturated with diisopropyl ether to give crystalline N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycine phenacyl ester (4.12 g.), which was recrystallized from ethanol to give the pure material, mp 125° to 126.5° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. filtrationThe insoluble substances were filtered off
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. dissolutionThe residual oil was dissolved in chloroform
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-f1238345f94141f9a9d61f085b2af688
Source dataset
uspto-grants-1981_04
Patent number
US04264498

Reaction notes

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