4-Methylmorpholine → HCID 53784856, compound

HRID 2268804Notes

Reaction equation

HRID 2268804 reaction equation
CCN=C=NCCCN(C)C.Cl.Cl.[CH3:14][O:15][C:16](=[O:27])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[NH2:18].[Cl:28][C:29]1[N:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](O)=[O:32].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[CH3:14][O:15][C:16](=[O:27])[C@H:17]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[NH:18][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][CH:36]=[N:37][C:29]=1[Cl:28]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 76956Methyl tyrosinate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 53784856HCID 53784856, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC.HCl (2.11 g, 11 mmol) was added to a mixture of L-tyrosine methyl ester hydrochloride (2.32 g, 10 mmol), 2-chloronicotinic acid (1.58 g, 10 mmol), HOBT (1.49 g, 11 mmol) and NMM (2.31 ml, 21 mmol) in DMF (50 ml). The mixture was stirred overnight at room temperature. The solvent was removed in vacuo. the residue dissolved in EtOAc (300 ml) and washed with dilute HCl (100 ml), saturated aqueous NaHCO3 (100 ml), water (3×100 ml) and brine (50 ml), dried (Na2SO4) and solvent removed in vacuo to give the title compound as a yellow gum (3.27 g, 98%). δH (DMSO-d6, 300 MHz) 9.21 (1H, s, OH), 9.03 (1H, d, J 7.9 Hz, CONH), 8.45 (1H, dd, J 4.8, 1.9 Hz, pyrH), 7.67 (1H, dd, J 7.4, 1.9 Hz, pyrH), 7.47 (1H, dd, J 7.5, 4.8 Hz, pyrH), 7.05 (2H, d, J 8.5 Hz, ArH), 6.67 (2H, d, J 8.5 Hz, ArH), 4.58 (1H, ddd, J 9.6, 7.9, 5.4 Hz, CHα), 3.65 (3H, s, CO2Me), 3.01 (1H, dd, J 13.9, 5.4 Hz, CHAHBAr) and 2.85 (1H, dd, J 13.9, 9.6 Hz, CHAHBAr), m/z (ESI, 60V) 335 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (300 ml)
  3. washwashed with dilute HCl (100 ml), saturated aqueous NaHCO3 (100 ml), water (3×100 ml) and brine (50 ml)
  4. dry with materialdried (Na2SO4) and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-cb248bf0a55d451a8d019808cac5bf9e
Source dataset
uspto-grants-2001_12
Patent number
US06329372B1

Reaction notes

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