Triethylamine → HCID 19818598, compound

HRID 1086934Notes

Reaction equation

HRID 1086934 reaction equation
[C:1](Cl)(=[O:6])[C:2]([O:4][CH3:5])=[O:3].[C:8]([C:11]1[CH:33]=[CH:32][C:14]([O:15][CH2:16][CH:17]([O:28][C:29](=[O:31])[CH3:30])[CH2:18][O:19][C:20]2[CH:21]=[C:22]([C:24]([CH3:27])=[CH:25][CH:26]=2)[NH2:23])=[C:13]([CH2:34][CH2:35][C:36]([F:39])([F:38])[F:37])[C:12]=1[OH:40])(=[O:10])[CH3:9].C(N(CC)CC)C>C(Cl)Cl>[C:8]([C:11]1[CH:33]=[CH:32][C:14]([O:15][CH2:16][CH:17]([O:28][C:29](=[O:31])[CH3:30])[CH2:18][O:19][C:20]2[CH:21]=[C:22]([NH:23][C:1](=[O:6])[C:2]([O:4][CH3:5])=[O:3])[C:24]([CH3:27])=[CH:25][CH:26]=2)=[C:13]([CH2:34][CH2:35][C:36]([F:38])([F:37])[F:39])[C:12]=1[OH:40])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 19818597HCID 19818597, compound

Product 1

HCID 19818598HCID 19818598, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.9 ml of methyl chlorooxalate in 8 ml of methylene chloride is added dropwise to a solution, cooled to 0°, of 8.3 g of 3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-2-acetoxy-propoxy-}-6-methyl-aniline and 2.9 ml of triethylamine in 70 ml of methylene chloride in the course of about 5 minutes and the mixture is then stirred at room temperature for a further 2 hours. The reaction mixture is poured onto ice-water and the organic phase is separated off. The methylene chloride phase is washed with water, dried over sodium sulfate and evaporated under reduced pressure. Methyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-2-acetoxy-propoxy}-6-methylphenyl}}-oxamate is thus obtained as an oil with an Rf value=0.13 (silica gel; toluene/ethyl acetate=6:1).

Workup

  1. additionThe reaction mixture is poured onto ice-water
  2. customthe organic phase is separated off
  3. washThe methylene chloride phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-86683322137347de8b7b9e6107bf69c7
Source dataset
uspto-grants-1991_07
Patent number
US05032606

Reaction notes

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