Dicyclohexylcarbodiimide → N-Cbz-1-aminocyclopropanecarboxylic acid 2,2,5,5-tetramethylcyclopentyl ester

HRID 35438Notes

Reaction equation

HRID 35438 reaction equation
[C:1]([NH:11][C:12]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[CH3:42][C:43]1([CH3:51])[CH2:47][CH2:46][C:45]([CH3:49])([CH3:48])[CH:44]1O>C(Cl)Cl>[CH3:42][C:43]1([CH3:51])[CH2:47][CH2:46][C:45]([CH3:49])([CH3:48])[CH:44]1[O:16][C:15]([C:12]1([NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:14][CH2:13]1)=[O:17]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 5516962,2,5,5-Tetramethylcyclopentan-1-olHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acid

Product 1

HCID 53791828N-Cbz-1-aminocyclopropanecarboxylic acid 2,2,5,5-tetramethylcyclopentyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-Cbz-1-aminocyclopropane carboxylic acid in dry (CH2)2Cl2 containing dicyclohexylcarbodiimide and dimethylaminopyridine (DMAP), all at 0° C., is added, via an addition funnel, 2,2,5,5-tetramethylcyclopentanol dissolved in CH2Cl2. After stirring for 4 days, the mixture is filtered, and the filtrate is washed with 5% HCl (1×50 ml), saturated NaHCO3 (1×50 ml), and water (1×50 ml). The organic layer is separated, dried over MgSO4 and evaporated to yield N-Cbz-1-aminocyclopropanecarboxylic acid 2,2,5,5-tetramethylcyclopentyl ester.

Workup

  1. additionall at 0° C., is added, via an addition funnel
  2. filtrationthe mixture is filtered
  3. washthe filtrate is washed with 5% HCl (1×50 ml), saturated NaHCO3 (1×50 ml), and water (1×50 ml)
  4. customThe organic layer is separated
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-210b0b7eb883423eb537680d49dd2b5a
Source dataset
uspto-grants-1988_08
Patent number
US04766246

Reaction notes

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