2-Dimethylaminopyridine → HCID 53860365, compound

HRID 2118461Notes

Reaction equation

HRID 2118461 reaction equation
[C:1]([NH:11][C:12]1([C:15]([OH:17])=O)[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].CN(C1C=CC=CN=1)C.[CH3:27][C:28]1([CH3:36])[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH:29]1[NH2:35]>C(Cl)Cl>[CH3:27][C:28]1([CH3:36])[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH:29]1[NH:35][C:15]([C:12]1([NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[CH2:13][CH2:14]1)=[O:17]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acidHCID 132479392,2,5,5-Tetramethylcyclopentanamine

Product 1

HCID 53860365HCID 53860365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-Cbz-1-aminocyclopropanecarboxylic acid in dry CH2Cl2 containing dicyclohexycarbodiimide and dimethylaminopyridine (DMAP), all at 0° C., is added, via an addition funnel, 2,2,5,5-tetramethyl-1-cyclopentyl amine dissolved in CH2Cl2. After stirring for 48 hours, 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 amide.

Workup

  1. filtrationthe mixture is filtered
  2. washthe filtrate is washed with 5% HCl (1×50 ml), saturated NaHCO3 (1×50 ml), and water (1×50 ml)
  3. customThe organic layer is separated
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-352b0e81519d4ff5b21c0a7f876cd254
Source dataset
uspto-grants-1987_07
Patent number
US04678674

Reaction notes

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