Tetrahydrofuran → HCID 10245053, compound

HRID 854506Notes

Reaction equation

HRID 854506 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]1[CH2:18][CH2:17][CH2:16]1)[CH:9]=[CH:8]2)[CH:2]=[CH2:3].[C:19](Cl)(=[O:23])[C:20](Cl)=[O:21].C1C[O:28]CC1>>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]1[CH2:18][CH2:17][CH2:16]1)[CH:9]=[C:8]2[C:19](=[O:23])[C:20]([OH:28])=[O:21])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 68550441HCID 68550441, compound

Product 1

HCID 10245053HCID 10245053, compound

Procedure

The crude 5-allyloxy-1-cyclobutylmethyl-1H-indole from Step 3 was dissolved in 0.5 mL anhydrous THF and 0.22 mL (2.5 mmol) oxalyl chloride was added. The reaction was mixed overnight on an orbital shaker. The reaction was concentrated and the crude product was redissolved in a minimum volume of dichloromethane. 0.8 mL 1N aqueous NaOH was added and the reaction was capped and shaken. The solution was acidified by the dropwise addition of 2N aqueous HCl and extracted with 1.6 mL dichloromethane. LC/MS (see Note 2) indicated that the reaction was not complete. The crude material was redissolved in 0.5 mL anhydrous THF, 0.16 mL oxalyl chloride was added, and the reaction was mixed at 40° C. for 6 hr with orbital shaking. The reaction was worked up as described previously and the crude products were purified by RP-HPLC (see Note 1) to afford 6.2 mg (19.8 μmol) (5-allyloxy-1-cyclobutylmethyl-1H-indol-3-yl)-oxo-acetic acid: LC/MS Data (molecular ion and retention time): m/z 312 (M−H); 2.49 min.

Workup

  1. additionThe reaction was mixed overnight on an orbital shaker
  2. concentrationThe reaction was concentrated
  3. dissolutionthe crude product was redissolved in a minimum volume of dichloromethane
  4. addition0.8 mL 1N aqueous NaOH was added
  5. customthe reaction was capped
  6. additionThe solution was acidified by the dropwise addition of 2N aqueous HCl
  7. extractionextracted with 1.6 mL dichloromethane
  8. dissolutionThe crude material was redissolved in 0.5 mL anhydrous THF
  9. addition0.16 mL oxalyl chloride was added
  10. additionthe reaction was mixed at 40° C. for 6 hr with orbital shaking
  11. customthe crude products were purified by RP-HPLC (see Note 1)

Sources & evidence

ORD record
ord-0527832946db44b08577fc485a34fad5
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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