1,2-Dichloroethane → HCID 54474227, compound

HRID 1740894Notes

Reaction equation

HRID 1740894 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[C:19]([C:21]1[CH:35]=[CH:34][C:24]([CH2:25][N:26]2[C:30]([CH2:31][CH2:32][NH2:33])=[CH:29][N:28]=[CH:27]2)=[CH:23][CH:22]=1)#[N:20].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C>[C:19]([C:21]1[CH:35]=[CH:34][C:24]([CH2:25][N:26]2[C:30]([CH2:31][CH2:32][NH:33][C:14]([C@@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13][N:8]3[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])=[CH:29][N:28]=[CH:27]2)=[CH:23][CH:22]=1)#[N:20]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 70193148HCID 70193148, compound

Product 1

HCID 54474227HCID 54474227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 -(t-Butyloxycarbonyl)-piperidine-2(S)-carboxylic acid (0.245 g, 1.07 mmol), 3-(4-cyanobenzyl) histamine dihydrochloride(0.320 g, 1.07 mmol), HOBT (0.137 g, 1.02 mmol), EDC (0.215 g, 1.12 mmol), Et3N (0.374 mL, 2.68 mmol) were dissolved in DMF (3 mL). The solution was stirred for 6 hr, then partitioned between EtOAc (20 mL) and satd NaHCO3 solution (20 mL). The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to dryness to give the title compound. 1H NMR (CDCl3); δ7.64 (d, 2H, J=9 Hz), 7.51 (s, 1H), 7.15 (d, 2H, J =9 Hz), 6.91 (s, 1H), 6.27 (br s, 1H), 5.23 (s, 2H), 4.66-4.73 (m, 1H), 3.95-4.16 (m, 1H), 3.41 q, 2H, J=6 Hz), 2.52-2.70 (m, 3H), 2.22-2.30 (m, 1H), 1.46 (s, 9H), 1.33-1.70 (m, 5H).

Workup

  1. custompartitioned between EtOAc (20 mL) and satd NaHCO3 solution (20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4448b2dc02814c87a7b040428c00271b
Source dataset
uspto-grants-1999_10
Patent number
US05972966

Reaction notes

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