Hydrochloric Acid → Cyclooct-1-yn-3-glycolic acid

HRID 45977Notes

Reaction equation

HRID 45977 reaction equation
N12CCCN=C1CCCCC2.Br[C:13]1[CH:20]([CH:21]([OH:26])[C:22]([O:24]C)=[O:23])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1.Cl>CS(C)=O>[C:18]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:20]([CH:21]([OH:26])[C:22]([OH:24])=[O:23])[C:19]#1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 66746412Methyl 2-bromocyclooctene-3-glycolate

Product 1

HCID 86653607Cyclooct-1-yn-3-glycolic acidYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

150 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 1 mmol) are added to a solution of methyl 2-bromocyclooctene-3-glycolate 17 (0.5 mmol) in anhydrous DMSO at 60° C. After stirring for 15 min, an additional 600 μl of DBU (4 mmol) are added and then the combined mixture is stirred overnight at 60° C. The mixture is acidified with 1M HCl and extracted with AcOEt. The organic phase is filtered through a separating filter and is concentrated under vacuum. The cyclooct-1-yn-3-glycolic acid 18 is purified on a preparative plate (CH2Cl2/MeOH 9/1) and is obtained with a yield of 55% (w=50 mg).

Workup

  1. stirringthe combined mixture is stirred overnight at 60° C
  2. extractionextracted with AcOEt
  3. filtrationThe organic phase is filtered through a separating
  4. filtrationfilter
  5. concentrationis concentrated under vacuum
  6. customThe cyclooct-1-yn-3-glycolic acid 18 is purified on a preparative plate (CH2Cl2/MeOH 9/1)
  7. customis obtained with a yield of 55% (w=50 mg)

Sources & evidence

ORD record
ord-5304446edd804e2994c754d9cb0a9933
Source dataset
uspto-grants-2013_09
Patent number
US08541604B2

Reaction notes

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