Hydrochloric Acid → (R-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid

HRID 1079301

Reaction equation

HRID 1079301 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C@H:9]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C@H:10]([OH:14])[C:11]([O-:13])=[O:12].C[C@H]([NH3+])C1C=CC=CC=1.Cl>O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C@H:9]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C@H:10]([OH:14])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86750040HCID 86750040, compound

Product 1

HCID 6451870(R-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acidYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve the (-)-salt 4 (42.85 g, 97.26 mmol) in boiling water (430 mL). Add hot 1N HCl (98 mL). Reflux for 1 min. Cool the mixture in an ice-water bath and stir vigourously to precipitate. Check (and adjust if necessary) the pH of the solution to 5.0 (pH meter). Collect the solid by filtration. Wash with water and dry in vacuo at 40° C. to obtain the title compound 5 (24.85 g, 80%). m.p. 175°-176° C. [α]D23 -362.8° (1.2 DMF).

Workup

  1. temperatureReflux for 1 min
  2. temperatureCool the mixture in an ice-water bath
  3. customto precipitate
  4. customCollect the solid
  5. filtrationby filtration
  6. washWash with water
  7. customdry in vacuo at 40° C.

Sources & evidence

ORD record
ord-91f5817949094ac49a86750469c7a62c
Source dataset
uspto-grants-1996_12
Patent number
US05580867

Linked notes

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