Hydrochloric Acid → HCID 18770669, compound

HRID 479477Notes

Reaction equation

HRID 479477 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].[OH-].[Na+].[C:12]1([CH3:21])[C:13]([C:18](Cl)=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1.Cl>O>[CH3:4][C:3]([CH3:6])([CH3:5])[CH:2]([NH:1][C:18](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH3:21])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 702762-Methylbenzoyl chlorideHCID 164608L-tert-Leucine

Product 1

HCID 18770669HCID 18770669, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Racemic tert-butylglycine (502 mg, 3.83 mmol) was dissolved in water (10 mL) containing NaOH (153 mg, 3.83 mmol). This solution was cooled to 5° C. and treated with o-toluoyl chloride (0.501 mL, 3.83 mmol) followed by additional NaOH (153 mg, 3.83 mmol). The mixture was warmed to ambient temperature, stirred for 1.5 hours, recooled to 5° C., and treated with 1M HCl (pH 3). The thick precipitate that formed was collected by filtration and washed with cold water to provide 550 mg of the desired product as a white solid.

Workup

  1. temperatureThe mixture was warmed to ambient temperature
  2. customrecooled to 5° C.
  3. customThe thick precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with cold water

Sources & evidence

ORD record
ord-77cf9615f2bc46b4859686eb481d6bc8
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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