1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86650119, compound

HRID 2179757Notes

Reaction equation

HRID 2179757 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][C@@H:14]([C:16]([OH:18])=O)[C:13]1([CH3:20])[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:42]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)[CH3:43]>C(Cl)Cl.CCN(CC)CC>[CH2:42]([N:44]1[CH2:49][CH2:48][N:47]([C:16]([C@@H:14]2[CH2:15][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:13]2([CH3:20])[CH3:19])=[O:18])[CH2:46][CH2:45]1)[CH3:43]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 791961-EthylpiperazineHCID 58111002HCID 58111002, compound

Product 1

HCID 86650119HCID 86650119, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of (1R,3S)-3-(benzyloxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (1.0 g) in DCM (30 ml) at 0° C. EDCI (800 mg) and HOBt (700 mg) were added, after 10 minutes N-Ethylpiperazine (800 mg) and Et3N (3 ml) were added drop wise and the reaction mass was allowed to stir at room temperature for 8 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water, saturated NaHCO3 solution, water, 1N HCl, water and saturated brine. The organic layer was concentrated under reduced pressure then the resulting crude was purified by silica gel column (100-200 mesh, elution 90% EtOAC in hexane) to afford the title compound as a syrup. Wt: 780 mg; Yield: 57.9%. 1H NMR and Mass complies with the required product.

Workup

  1. customat 0° C
  2. additionwere added drop wise
  3. customAfter completion of the reaction (monitored by TLC)
  4. washwashed with water, saturated NaHCO3 solution, water, 1N HCl, water and saturated brine
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting crude was purified by silica gel column (100-200 mesh, elution 90% EtOAC in hexane)

Sources & evidence

ORD record
ord-c70922f657844bf1a58b158b400cc223
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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