Acetic Acid → HCID 57339402, compound

HRID 444622Notes

Reaction equation

HRID 444622 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].O[N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C>C1COCC1>[O:15]=[C:10]1[CH2:11][CH2:12][C:13](=[O:14])[N:9]1[O:6][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 57339402HCID 57339402, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

4-pentynoic acid (5.0 g, 51 mmol) and N-hydroxy succinimide (5.87 g, 51 mmol) were added to a solution of DCC (12.6 g, 61.2 mmol) in THF (125 ml) at −10° C. The mixture was then stirred for 1 h at −10° C. then left to stir at room temperature overnight. (A white precipitate was observed after 15 min). Acetic acid (0.63 ml) was then added. The resulting DCU was removed by filtration. The filtrate was then evaporated to give 10a (10 g, 100% crude yield).

Workup

  1. waitthen left
  2. stirringto stir at room temperature overnight
  3. wait(A white precipitate was observed after 15 min
  4. customThe resulting DCU was removed by filtration
  5. customThe filtrate was then evaporated

Sources & evidence

ORD record
ord-16c9bb3b940c42ca96f547030d38d13f
Source dataset
uspto-grants-2013_07
Patent number
US08475768B2

Reaction notes

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