Dicyclohexylcarbodiimide → HCID 58542422, compound

HRID 1951910Notes

Reaction equation

HRID 1951910 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([NH:23][C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:30]([O:37][C:38]([NH:40][C:41]1([C:44](O)=[O:45])[CH2:43][CH2:42]1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl>[CH2:16]([N:23]([C:44]([C:41]1([NH:40][C:38]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])[CH2:42][CH2:43]1)=[O:45])[C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acidHCID 10535780(S)-methyl 2-(benzylamino)propanoate

Product 1

HCID 58542422HCID 58542422, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N′-dicyclohexylcarbodiimide (6.0 g, 29.0 mmol) was added to a dichloromethane (150 ml) solution of methyl N-benzyl-L-alaninate (5.20 g, 26.9 mmol) and 1-{[(benzyloxy)carbonyl]amino}cyclopropanecarboxylic acid (6.30 g, 26.7 mmol) under ice cooling and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and then diluted with ethyl acetate, insoluble matter was removed by filtration and then the filtrate was washed with 1 N aqueous hydrochloric acid solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:3 (v/v)] to give the title compound (7.80 g, 71%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate, insoluble matter
  3. customwas removed by filtration
  4. washthe filtrate was washed with 1 N aqueous hydrochloric acid solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:3 (v/v)]

Sources & evidence

ORD record
ord-a20576f1588845bb921f80a3459610b8
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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