Resorcinol → HCID 20312442, compound

HRID 2420009Notes

Reaction equation

HRID 2420009 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 3 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-ba5ee328caa8414a8cdc7d8f8b94cf3d
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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