Dicyclohexylcarbodiimide → HCID 68137584, compound

HRID 1605188Notes

Reaction equation

HRID 1605188 reaction equation
[CH3:1][C:2]1([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH3:24][O:25][C:26](=[O:30])[C@H:27]([CH3:29])[NH2:28].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C.C(N(CC)CC)C>[CH3:1][C:2]1([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1.[CH3:24][O:25][C:26](=[O:30])[C@H:27]([CH3:29])[NH2:28]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2733257Alanine methyl ester hydrochlorideHCID 54520100HCID 54520100, compound

Product 1

HCID 68137584HCID 68137584, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

To a solution of 0.52 mM of N-(1-methylcyclohexyloxycarbonyl) phenylalanine in 4 ml. acetonitrile is added 0.60 mM alanine methyl ester hydrochloride and 80 microliters of triethylamine. Immediately following addition of the triethylamine, a solution of 0.58 mM of N,N'-dicyclohexylcarbodiimide in 2 ml. of acetonitrile is added and the reaction is allowed to stir overnight at 20°-25°C. Excess N,N'-dicyclohexylcarbodiimide is destroyed by addition of 5 drops of 50% acetic acid. After adding 15 ml. of methylenechloride, the reaction mixture is filtered to remove the dicyclohexylurea formed during the reaction and the filtrate is treated in the following manner: wash with saturated sodium bicarbonate, 50% saturated sodium chloride solution, 0.2 N sulfuric acid saturated with sodium sulfate, twice with 50% saturated sodium chloride solution. Repeat washing cycle with two portions of methylene chloride and dry over sodium sulfate. The solvent is removed and substantially pure N-(1-methylcyclohexyloxycarbonyl) phenylalanine-alanine methyl ester is obtained.

Workup

  1. customExcess N,N'-dicyclohexylcarbodiimide is destroyed by addition of 5 drops of 50% acetic acid
  2. additionAfter adding 15 ml
  3. filtrationof methylenechloride, the reaction mixture is filtered
  4. customto remove the dicyclohexylurea
  5. customformed during the reaction
  6. additionthe filtrate is treated in the following manner
  7. washwash with saturated sodium bicarbonate, 50% saturated sodium chloride solution, 0.2 N sulfuric acid saturated with sodium sulfate, twice with 50% saturated sodium chloride solution
  8. washRepeat washing cycle with two portions of methylene chloride
  9. dry with materialdry over sodium sulfate
  10. customThe solvent is removed

Sources & evidence

ORD record
ord-eed55eb298a54410b2a80a6ebaaedded
Source dataset
uspto-grants-1976_04
Patent number
US03948971

Reaction notes

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