Methanol → 2-[({3-[(4-Methoxyphenyl)diphenylamino]propyl}oxycarbonyl)methoxy]-acetic acid, triethylammonium salt

HRID 47966Notes

Reaction equation

HRID 47966 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][CH2:18][OH:19])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:33]([O:37][C:38](=O)[CH2:39][OH:40])(=O)[CH2:34][OH:35].C[OH:43]>C(Cl)Cl>[CH2:10]([NH+:15]([CH2:20][CH3:21])[CH2:16][CH3:17])[CH3:9].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][CH2:18][O:19][C:34]([CH2:33][O:37][CH2:38][C:39]([O-:40])=[O:43])=[O:35])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10034680Acetic acid, hydroxy-, anhydrideHCID 667170843-[(4-Methoxyphenyl)diphenylamino]propan-1-ol

Product 1

HCID 1317242222-[({3-[(4-Methoxyphenyl)diphenylamino]propyl}oxycarbonyl)methoxy]-acetic acid, triethylammonium salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.72 g (7.83 mmol) of the alcohol (26) was dissolved in 20 mL of methylene chloride with 1.3 mL (9.4 mmol) of triethylamine and 1.1 g (9.5 mmol) of glycolic anhydride. The mixture was stirred for 2 h (became homogeneous). TLC showed clean reaction (Rf=0.35 in 9:1/methylene chloride:methanol). The solvents were removed by evaporation and the residue was chromatographed on a 1.5×18 inch silica gel column packed with 93% methylene chloride, 5% methanol, and 2% triethylamine. The fractions containing product were combined and solvent was removed by evaporation. Co-evaporation with dry DMF ensured removal of traces of water and of residual volatile solvents. Yield of the colorless syrup (27) was assumed to be 100%. The syrup was dissolved in dry DMF to give a final volume of 23.4 mL (˜0.33 M solution).

Workup

  1. customThe solvents were removed by evaporation
  2. customthe residue was chromatographed on a 1.5×18 inch silica gel column
  3. additionThe fractions containing product
  4. customsolvent was removed by evaporation
  5. customCo-evaporation with dry DMF
  6. customremoval of traces of water
  7. dissolutionThe syrup was dissolved in dry DMF

Sources & evidence

ORD record
ord-e8e3b633554542c6b9f84ccd7228bb5c
Source dataset
uspto-grants-2004_03
Patent number
US06699975B2

Reaction notes

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