Ethylmorpholine → HCID 70000822, compound

HRID 1634849Notes

Reaction equation

HRID 1634849 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.Cl.CN(C)CCCN=C=NCC.C(N1CCOCC1)C.OC1C2N=NNC=2C=CC=1.Cl.[CH2:52]([O:54][C:55](=[O:62])[C@H:56]([CH2:58][CH:59]([CH3:61])[CH3:60])[NH2:57])[CH3:53]>C1COCC1>[CH2:52]([O:54][C:55](=[O:62])[C@@H:56]([NH:57][C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([N:7]2[CH2:6][CH2:5][CH:4]([CH:3]([O:2][CH3:1])[O:19][CH3:20])[CH2:9][CH2:8]2)=[CH:18][CH:17]=1)[CH2:58][CH:59]([CH3:60])[CH3:61])[CH3:53]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)HCID 18678400HCID 18678400, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 70000822HCID 70000822, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-(dimethoxymethyl)piperidinyl)benzoic acid (0.450 g, 1.6 mmol), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide HCl (0.340 g, 1.77 mmol), N-ethyl morpholine (0.50 mL, 3.9 mmol), hydroxybenzotriazole (0.239 g, 1.77 mmol), and L-leucine ethyl ester HCl (0.322 g, 1.8 mmol) in THF (15 mL) was stirred at ambient temperature overnight. The solvent was evaporated in vacuo and the residue was dissolved in methylene chloride. The organic phase was washed with 1N HCl, 1N NaOH, brine and dried (Na2SO4). The solvent was evaporated in vacuo and the residue purified by flash chromatography (methylene chloride-methanol, 19:1) to give 0.163 g of the title compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe organic phase was washed with 1N HCl, 1N NaOH, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe residue purified by flash chromatography (methylene chloride-methanol, 19:1)

Sources & evidence

ORD record
ord-a14c6860aeef4d52897cee4e5711a41b
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…