Acetic Acid → HCID 54030218, compound

HRID 257511Notes

Reaction equation

HRID 257511 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][OH:19].C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C>C(OCC)(=O)C>[OH: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 80641,4-ButanediolHCID 10868DicyclohexylcarbodiimideHCID 3035658(5-(3-Thienyl)tetrazol-1-yl)acetic acid

Product 1

HCID 54030218HCID 54030218, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1 g (4.76 mM) of [5-(3-thienyl) tetrazol-1-yl]acetic acid and 514 mg (5.71 mM) of 1,4-butanediol in 20 ml of ethyl acetate 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 filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (eluent; chloroform/ethyl alcohol=30/1) for separation and purification, to give 520 mg (yield 38.7%) of [5-(3-thienyl)tetrazol-1-yl]acetic acid 4-hydroxybutyl ester.

Workup

  1. stirringwas stirred for 30 min
  2. filtrationThe mixture was filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was subjected to silica gel column chromatography (eluent; chloroform/ethyl alcohol=30/1) for separation and purification

Sources & evidence

ORD record
ord-e4fe96207efa43c19b354c5866ef3590
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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