Hydroxyphenylacetic acid → HCID 19974159, compound

HRID 1587932Notes

Reaction equation

HRID 1587932 reaction equation
[OH:1][CH:2]([C:5]1[N:6]=[C:7]([CH3:10])[S:8][CH:9]=1)[CH2:3][NH2:4].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](O)=[O:20])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>O1CCCC1>[OH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[N:6]=[C:7]([CH3:10])[S:8][CH:9]=2)=[O:20])=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 127Hydroxyphenylacetic acidHCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 167684962-Amino-1-(2-methyl-1,3-thiazol-4-yl)ethanol

Product 1

HCID 19974159HCID 19974159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.16 g (20 mmol) of 2-Hydroxy-2-(2-methyl-thiazol-4-yl)ethanamine are dissolved in 80 ml of absolute tetrahydrofuran and, successively, 3.84 g (20 mmol) of 4-hydroxy-phenylacetic acid, 6.3 g (24 mmol) of triphenylphosphine, 5.6 ml (40 mmol) of triethylamine and 2 ml (20 mmol) of carbon tetrachloride are added. After stirring overnight, the mixture is concentrated, the residue is taken up in 2N hydrochloric acid and the solution is extracted three times with methylene chloride. The aqueous phase is then adjusted to pH 7 with 2N sodium hydroxide solution and evaporated to dryness. The residue from evaporation is extracted by boiling several times with a mixture of chloroform/methanol (1:1). The extracts are concentrated, and the residue is purified on a silica gel column using ethyl acetate/methanol=50:1 as eluant.

Workup

  1. concentrationthe mixture is concentrated
  2. extractionthe solution is extracted three times with methylene chloride
  3. customevaporated to dryness
  4. customThe residue from evaporation
  5. extractionis extracted
  6. additionwith a mixture of chloroform/methanol (1:1)
  7. concentrationThe extracts are concentrated
  8. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-5d3dfa77e0e24d0cadc6acb0a9cdedd6
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

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