Hydrochloric Acid → HCID 9992929, compound

HRID 397248Notes

Reaction equation

HRID 397248 reaction equation
C1(C(Cl)=O)CCCCC1.N[C@H](C(O)=O)CC(C)C.Cl.[Na+].[CH:21]1([C:27]([NH:29][C@H:30]([C:35]([O-:37])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[Na+].C1(C([O-])=O)CCCCC1.[Na+].C1(C(N[C@H](C(N[C@H](C([O-])=O)CC(C)C)=O)CC(C)C)=O)CCCCC1>[OH-].[Na+]>[CH:21]1([C:27]([NH:29][C@H:30]([C:35]([OH:37])=[O:36])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6106L-LeucineHCID 75938Cyclohexanecarbonyl chlorideHCID 23666323HCID 23666323, compoundHCID 23669769HCID 23669769, compoundHCID 23673627Sodium cyclohexanecarboxylate

Product 1

HCID 9992929HCID 9992929, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

Cyclohexanoyl chloride (32.7 mL, 232 mmole) was added dropwise to a solution of (L)-leucine (37 g, 282 mmole) in aqueous sodium hydroxide (500 mL, 2 N). During the course of this addition, the reaction temperature was maintained below 45° C. using an ice/water bath, as necessary. The pH was maintained at about 10 by the addition of aliquots of 14 N NaOH, as necessary. After the addition was complete, the reaction mixture was stirred for an additional 2 hours at room temperature. The resulting clear solution was adjusted to pH 2.5 by the dropwise addition of concentrated hydrochloric acid. The precipitate was collected by filtration, re-dissolved in a minimum amount of 12 N sodium hydroxide, and re-precipitated by dropwise addition of concentrated hydrochloric acid and filtered. The crude reaction product was a white solid and contained about 85% N-cyclohexanoyl leucine sodium salt, about 10% cyclohexane carboxylic acid sodium salt, and about 5 N-cyclohexanoylleucylleucine sodium salt, by weight. The solid was washed with dilute aqueous hydrochloric acid (750 mL, 0.1 N) to provide N-cyclohexanoyl-(L)-leucine as a white crystalline solid (52.6 g, 77%).

Workup

  1. additionDuring the course of this addition
  2. temperaturethe reaction temperature was maintained below 45° C.
  3. additionAfter the addition
  4. filtrationThe precipitate was collected by filtration
  5. dissolutionre-dissolved in a minimum amount of 12 N sodium hydroxide
  6. customre-precipitated by dropwise addition of concentrated hydrochloric acid
  7. filtrationfiltered
  8. customThe crude reaction product
  9. washThe solid was washed with dilute aqueous hydrochloric acid (750 mL, 0.1 N)

Sources & evidence

ORD record
ord-7cd8b7b474994630abff1563e7f9aad8
Source dataset
uspto-grants-2003_08
Patent number
US06610329B2

Reaction notes

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