Acetic Acid → HCID 54541157, compound

HRID 257509Notes

Reaction equation

HRID 257509 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:10]([CH2:11][C:12]([OH:14])=[O:13])[N:9]=[N:8][N:7]=2)=[CH:2]1.[CH2:15](O)[CH2:16][CH2:17][OH:18].C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C>CN(C)C=O>[OH:18][CH2:17][CH2:16][CH2:15][O:13][C:12](=[O:14])[CH2:11][N:10]1[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[N:7][N:8]=[N:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 104421,3-PropanediolHCID 10868DicyclohexylcarbodiimideHCID 3035658(5-(3-Thienyl)tetrazol-1-yl)acetic acid

Product 1

HCID 54541157HCID 54541157, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg (2.38 mM) of [5-(3-thienyl) tetrazol-1-yl] acetic acid and 220 mg (2.85 mM) of 1,3-propanediol in 5 ml of N,N-dimethylformamide was added 540 mg (2.62 mM) of dicyclohexylcarbodiimide at room temperature. After the mixture was stirred at room temperature for 30 min, a small amount of acetic acid was added to the mixture and then was stirred for 30 min. The mixture was poured into ice-water. The precipitated crystal was filtered off and washed with water. The filtrate was extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (eluent: chloroform/ethyl alcohol=60/1) for separation and purification, to give 350 mg (yield 54.8%) of [5-(3-thienyl) tetrazol-1-yl] acetic acid 3-hydroxypropyl ester.

Workup

  1. stirringwas stirred for 30 min
  2. filtrationThe precipitated crystal was filtered off
  3. washwashed with water
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was subjected to silica gel column chromatography (eluent: chloroform/ethyl alcohol=60/1) for separation and purification

Sources & evidence

ORD record
ord-d285f4b9a0a34588900a36634ce42957
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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