Methanol → HCID 53845088, compound

HRID 651182Notes

Reaction equation

HRID 651182 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH2:17][CH2:18][N:19]=2)=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:20]O>S(Cl)(Cl)=O>[CH3:20][O:6][C:5](=[O:7])[CH:4]([NH2:3])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:19][CH2:18][CH2:17][N:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 23458864HCID 23458864, compound

Product 1

HCID 53845088HCID 53845088, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

(±)-2-Amino-3-[4-(4,5-dihydro-1H-imidazol-2-yl)-phenyl]-propionic acid dihydrochloride (0.50 g, 1.6 mmol) was placed in thionyl chloride (1 mL) and methanol (25 mL). The mixture was heated to reflux for 30 minutes, at which time more thionyl chloride (3 mL) and methanol (75 mL) were added. After another 3 hours at reflux, the solution was concentrated, the residue was dissolved in a small amount of methanol and ethyl acetate was added to induce precipitation. The solid was collected and dried (0.40 g, mp 230° C. dec.).

Workup

  1. temperatureThe mixture was heated
  2. additionwere added
  3. temperatureAfter another 3 hours at reflux
  4. concentrationthe solution was concentrated
  5. dissolutionthe residue was dissolved in a small amount of methanol and ethyl acetate
  6. additionwas added
  7. customprecipitation
  8. customThe solid was collected
  9. customdried (0.40 g, mp 230° C. dec.)

Sources & evidence

ORD record
ord-0f1fe9e0e95c4759ac8ab3e12af22516
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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