Thioglycerol → HCID 66637835, compound

HRID 1095005Notes

Reaction equation

HRID 1095005 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:8]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:7][C:6]=1[NH:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Cl)[CH:24]=1)[CH3:2].C(N(CC)CC)C.[SH:40][CH2:41][CH:42]([OH:45])[CH2:43][OH:44].ClCC1C=C(C=CC=1)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:8]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:7][C:6]=1[NH:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][S:40][CH2:41][CH:42]([OH:45])[CH2:43][OH:44])[CH:24]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7291ThioglycerolHCID 8471TriethylamineHCID 2417523-(Chloromethyl)benzoic acidHCID 666392362-(3-Chloromethylbenzoylamino)-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester

Product 1

HCID 66637835HCID 66637835, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, 2-(3-chloromethyl-benzoylamino)-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (1.1 g) was dissolved in anhydrous methylene chloride (20 ml). Triethylamine (800 μl) and 3-mercapto-1,2-propanediol (compound B′) (600 μl) were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 36 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-[3-(2,3-dihydroxy-propylsulfanylmethyl)-benzoylamino]-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (970 mg, yield 77%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was then subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluted with a chloroform-methanol system

Sources & evidence

ORD record
ord-92b06e8470e846048dcfede94456265a
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

Loading…