Resorcinol → HCID 20312442, compound

HRID 1973482Notes

Reaction equation

HRID 1973482 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH2:9]([O:13][C:14](=[O:28])[CH:15](OC(=O)C)[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH2:11][CH3:12].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:9]([O:13][C:14](=[O:28])[CH:15]([C:6]1[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=1[OH:5])[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 8000Boron trifluoride etherateHCID 20312395HCID 20312395, compound

Product 1

HCID 20312442HCID 20312442, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 11.0 g. (0.1 mol.) of resorcinol and 24.7 g. (0.085 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester in 250 ml. of methylene chloride at 0° was added 1 ml. of boron trifluoride etherate. The reaction mixture was allowed to warm to room temperature during a 30 minute period, then it was stirred for an additional three hours. The reaction mixture was washed five times with equal volumes of water, dried (Na2SO4) and concentrated in vacuo to give N-t-butoxycarbonyl-2-(2,4-dihydroxyphenyl)glycine n-butyl ester.

Workup

  1. additionTo a stirred mixture of 11.0 g
  2. washThe reaction mixture was washed five times with equal volumes of water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f83e2bd7ce148cb846a298b1dd6eea3
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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