1,2-Dichloroethane → HCID 70081974, compound

HRID 840739Notes

Reaction equation

HRID 840739 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([NH:25][C@H:26]([C:31](O)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:31](=[O:32])[C@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:25][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 757711-HydroxybenzotriazoleHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 70081974HCID 70081974, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyl-4-amino piperidine (0.50 g) in CH2Cl2 (10 mL) was added CBZ-leucine (695 mg), EDC (552.5 mg) and HOBT (356.6 mg). The reaction was stirred at room temperature until complete as indicated by TLC analysis. The reaction was dissolved in CHCl3 and washed with 10% Na2CO3, brine, dried (MgSO4), filtered, concentrated and chromatographed (3:1 EtOAc:hexanes) to give 0.99 g of the title compound: MS(ES+) 438 (MH+).

Workup

  1. washwashed with 10% Na2CO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (3:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-0c503050f99f43b2ba8c32d5a1d54ac0
Source dataset
uspto-grants-2002_04
Patent number
US06369077B1

Reaction notes

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