Triethylamine → Ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-(carbethoxyethylthio)ethyl)phenoxy)acetate

HRID 2073908Notes

Reaction equation

HRID 2073908 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19](O)[CH2:20][C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:16]=[CH:17][CH:18]=1.O=S(Cl)Cl.[SH:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43].C(N(CC)CC)C>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]([S:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:20][C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21625Ethyl 3-mercaptopropionateHCID 24386Thionyl ChlorideHCID 14774138Ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-hydroxyethyl)phenoxy)acetate

Product 1

HCID 14774139Ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-(carbethoxyethylthio)ethyl)phenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product obtained from Step C in 50 mL of CH2Cl2 is treated with 2 mL of SOCl2. The reaction mixture is stirred at room temperature for 2 hr. and then evaporated to dryness. The crude product thus obtained in 20 mL of CH2Cl2 is treated with ethyl 3-mercaptopropionate and triethylamine (1:1) for 16 hr. at room temperature. After evaporation of solvent, the crude product is purified by flash column chromatography to obtain ethyl 2-(3-(2-(3-(2-quinolinylmethyloxy)phenyl)-2-(carbethoxyethylthio)ethyl)phenoxy)acetate.

Workup

  1. customand then evaporated to dryness
  2. customThe crude product thus obtained in 20 mL of CH2Cl2
  3. customat room temperature
  4. customAfter evaporation of solvent
  5. customthe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-3f407f963e5e4525a20197cbeb3b659a
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

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