Phenol → HCID 20312393, compound

HRID 1973487Notes

Reaction equation

HRID 1973487 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([C:24]1[CH:25]=[CH:26][C:21]([OH:27])=[CH:22][CH:23]=1)[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:2][CH2:3][CH3:4].[CH2:1]([O:5][C:6](=[O:20])[CH:7]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[OH:27])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 996PhenolHCID 8000Boron trifluoride etherateHCID 20312395HCID 20312395, compound

Product 2

HCID 20312393HCID 20312393, compoundHCID 20312394N-t-butoxycarbonyl-2-(4-hydroxyphenyl)glycine n-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.5 g. (0.005 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester in 10 ml. of methylene chloride was slowly added over a one hour period to a stirred solution of 0.6 g. (0.006 mol.) of phenol and 0.1 ml. of boron trifluoride etherate in 15 ml. of methylene chloride. After three hours the reaction mixture was chromatographed on 50 g. of silica gel and eluted with methylene chloride containing increasing amounts of ethyl acetate to give N-t-butoxycarbonyl-2-(4-hydroxyphenyl)-glycine n-butyl ester and N-t-butoxycarbonyl-2-(2-hydroxyphenyl)glycine n-butyl ester.

Workup

  1. customAfter three hours the reaction mixture was chromatographed on 50 g
  2. washof silica gel and eluted with methylene chloride containing
  3. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-99996877c49847c392eee5ccc2f2b8bf
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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