L-Leucine → N,N'-Dicyclohexylurea

HRID 325941Notes

Reaction equation

HRID 325941 reaction equation
Cl.N[C@H](C(OC)=[O:9])CC(C)C.N[C@H](C(O)=O)CC(C)C.CCC(OC(C[N+](C)(C)C)CC([O-])=O)=O.[CH:36]1([N:42]=[C:43]=[N:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>CC(C)=O.N1C=CC=CC=1>[C:43]([NH:42][CH:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1)([NH:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1)=[O:9]

Participants

7

Reactant 4

HCID 6106L-LeucineHCID 10868DicyclohexylcarbodiimideHCID 1077383-(Propanoyloxy)-4-(trimethylazaniumyl)butanoateHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 1049PyridineSolvent

Procedure

To 1.82 grams (0.01 moles) of methyl leucinate hydrochloride 0.8 cc (0.01 moles) of pyridine in 15 cc of acetone were added. Pyridine hydrochloride precipitated, which was filtered off. To the methyl ester of leucine free base was added an aqueous solution of 2.54 grams (0.01 moles) of propionyl carnitine in 3.5 cc. Then, 4.12 grams of dicyclohexyl carbodiimide dissolved in 5 cc of acetone were slowly added under stirring to the solution. A precipitate of dicyclohexylurea formed which after 16 hours was filtered off. The mother liquors were concentrated under vacuum. The raw product thus obtained was crystallized from methanol-acetone, furnishing a solid, very hygroscopic product (yield: 75%).

Workup

  1. customPyridine hydrochloride precipitated
  2. filtrationwhich was filtered off
  3. additionwere slowly added

Sources & evidence

ORD record
ord-dd38be54ca81470fb9dd02a98629ec54
Source dataset
uspto-grants-1984_04
Patent number
US04443475

Reaction notes

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