Acetic Acid → HCID 54294640, compound

HRID 257512Notes

Reaction equation

HRID 257512 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][CH2:18][CH2:19][OH:20].C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C>CN(C)C=O>[OH:20][CH2:19][CH2:18][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 81051,5-PentanediolHCID 10868DicyclohexylcarbodiimideHCID 3035658(5-(3-Thienyl)tetrazol-1-yl)acetic acid

Product 1

HCID 54294640HCID 54294640, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g (4.76 mM) of [5-(3-thienyl)tetrazol-1-yl]acetic acid and 590 mg (5.71 mM) of 1,5-pentanediol in 10 ml of N,N-dimethylformamide was added 1.08 g (5.23 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=60/0) for separation and purification, to give 670 mg (yield 47.5%) of [5-(3-thienyl)tetrazol-1-yl]acetic acid 5-hydroxypentyl 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=60/0) for separation and purification

Sources & evidence

ORD record
ord-30102317ea634d6589832196e261d066
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

Loading…