Methanol → HCID 178500074, compound

HRID 1056840Notes

Reaction equation

HRID 1056840 reaction equation
[OH:1][C:2]1[C:3]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:4]=2[N:5]=[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[N:7]=1.S(=O)(=O)(O)O.[CH3:25]O>>[CH3:25][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:6]1[N:7]=[C:2]([OH:1])[C:3]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:4]=2[N:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178525368HCID 178525368, compound

Product 1

HCID 178500074HCID 178500074, compoundYield 63%

Procedure

To a solution of 3-(4-hydroxy-5,6,7,8-tetrahydro-[1]benzothiopheno[2,3-d]pyrimidin-2-yl)-propionic acid (3 g, 0.01 mol) in methanol (15 ml) was added catalytic amount of sulphuric acid (0.2 ml) and the solution was refluxed for 2 hrs. The methanol was distilled off, and the residue was washed with sodium bicarbonate solution to give 2 g (63%) of 3-(4-hydroxy-5,6,7,8-tetrahydro-[1]benzothiopheno[2,3-d]pyrimidin-2-yl)-propionic acid methyl ester as an off-white solid, which was used without further purification. 1H NMR (400 MHz, DMSO) δ ppm=1.73 (m, 4H), 2.6 (m, 2H), 2.78 (m, 2H), 2.83 (m, 4H), 3.37 (s, 3H), 12.18 (s, 1H). LC-MS: [M+H]=293.3.

Workup

  1. temperaturethe solution was refluxed for 2 hrs
  2. distillationThe methanol was distilled off
  3. washthe residue was washed with sodium bicarbonate solution

Sources & evidence

ORD record
ord-ccb239cae58e4019b656c4fff52b1398
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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