Hydrochloric Acid → HCID 29900805, compound

HRID 1482444Notes

Reaction equation

HRID 1482444 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.Cl>O1CCCC1.O>[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])=[O:20])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5951L-SerineHCID 11430Potassium Carbonate2×HCID 134054-Methylbenzoyl Chloride

Product 1

HCID 29900805HCID 29900805, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

L-Serine (100 g, 0.952 mol) (Wako Pure Chemical Industries, Ltd.), potassium carbonate (131.5 g, 0.952 mol) (Wako Pure Chemical Industries, Ltd.), and water 1 L were placed into a recovery flask (egg plant flask), followed by stirring vigorously. p-Methylbenzoyl chloride prepared in Step 1 was dissolved in tetrahydrofuran (Wako Pure Chemical Industries, Ltd.), which was added dropwise to this solution for 30 minutes. During this process, pH was maintained in the vicinity of 8 while additionally adding potassium carbonate. After the completion of the dropwise addition, the agitation was performed for 1 hour. The reaction solution was added to water 1 L which was prepared in a distinct vessel, and then pH was adjusted to not more than 3 with hydrochloric acid, followed by being cooled to 4° C. Precipitated crystals were filtrated, followed by being recrystallized with a mixed solvent of ethanol (Wako Pure Chemical Industries, Ltd.)/water=6/4. An objective substance was obtained in an amount of 106.0 g (yield: 64.7%).

Workup

  1. additionwhich was added dropwise to this solution for 30 minutes
  2. additionAfter the completion of the dropwise addition
  3. customwas prepared in a distinct vessel
  4. customPrecipitated crystals
  5. filtrationwere filtrated
  6. customby being recrystallized with a mixed solvent of ethanol (Wako Pure Chemical Industries, Ltd.)/water=6/4
  7. customAn objective substance was obtained in an amount of 106.0 g (yield: 64.7%)

Sources & evidence

ORD record
ord-e575ee07ea0f42a7aa145014555ae3c2
Source dataset
uspto-grants-2016_08
Patent number
US09414998B2

Reaction notes

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