Triethylamine → HCID 10374617, compound

HRID 2377292Notes

Reaction equation

HRID 2377292 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].C(Cl)(=O)C(Cl)=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.CCN(CC)CC>C1COCC1.CN(C=O)C>[C:1]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:7])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 224644-Pentynoic acidHCID 31268PyrrolidineHCID 65578Oxalyl chloride

Product 1

HCID 10374617HCID 10374617, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-pentynoic acid (981 mg, 10 mmol) in THF (40 mL) and DMF (2 drops) was added dropwise oxalyl chloride (0.96 mL, 11 mmol) over 10 min. The solution was stirred for 3 h at rt, then the flask was cooled in an ice bath and a solution of pyrrolidine (1.65 mL, 20 mmol) and Et3N (1.74 mL, 12.5 mmol) in THF (10 mL) was added dropwise over 17 min. The resulting suspension was stirred overnight, then filtered. The filtrate was partitioned between EtOAc (300 mL) and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to dryness, giving the desired product as a brown solid (1.32 g, 87%). MS (APCI(+)) m/e 152.1 (M+H)+.

Workup

  1. temperaturethe flask was cooled in an ice bath
  2. stirringThe resulting suspension was stirred overnight
  3. filtrationfiltered
  4. customThe filtrate was partitioned between EtOAc (300 mL) and H2O
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-847056bff2634a819a09b191e262c63a
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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