Propylene Glycol → HCID 46853062, compound

HRID 1258122Notes

Reaction equation

HRID 1258122 reaction equation
[CH3:1][C@:2]12[C:9]([CH3:11])([CH3:10])[C@:6]([NH:12]C(=O)C)([CH2:7][CH2:8]1)[CH2:5][O:4][CH2:3]2.N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.C(O)C(O)C>C1COCC1>[CH3:1][C@:2]12[C:9]([CH3:11])([CH3:10])[C@:6]([NH2:12])([CH2:7][CH2:8]1)[CH2:5][O:4][CH2:3]2

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 57518631HCID 57518631, compound

Product 1

HCID 46853062HCID 46853062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of step 3 intermediate (0.165 g, 0.78 mmol) in 3 mL of dry THF and pyridine (0.37 mL, 47 mmol) maintained at 0° C., oxalyl chloride was added with stirring. After 30 minutes propylene glycol (0.46 mL, 63 mmol) was added to the above reaction mixture and reaction warmed to room temperature. Reaction mixture was concentrated after adding ethyl alcohol. The residue was partitioned between 1N HCl and tert-butyl ether. Aqueous layer was separated and basified with 4N NaOH and extracted with ethyl acetate. Ethyl acetate layer was separated, dried and concentrated. Crude material was carried to next step without further purification. m/z (M+1): 170.2.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additionafter adding ethyl alcohol
  4. customThe residue was partitioned between 1N HCl and tert-butyl ether
  5. customAqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. customEthyl acetate layer was separated
  8. customdried
  9. concentrationconcentrated
  10. customCrude material was carried to next step without further purification

Sources & evidence

ORD record
ord-04d96f3dc26e42f2a9baedb7ff9ec5f6
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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