1,2-Dichloroethane → HCID 86584722, compound

HRID 2268800Notes

Reaction equation

HRID 2268800 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:10][CH:9]=1)[NH2:6].[Cl:25][C:26]1[N:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](O)=[O:29].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:12][CH:13]=1)[NH:6][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[N:34][C:26]=1[Cl:25]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 69806827HCID 69806827, compound

Product 1

HCID 86584722HCID 86584722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of O-(2,6-dichlorobenzyl)-L-tyrosine methyl ester hydrochloride, (1.11 g, 2.84 mmol), 2-chloronicotinic acid (0.45 g, 2.84 mmol), EDC (0.60 g, 3.13 mmol), HOBT (0.46 g, 3.41 mmol) and NMM (0.467 ml, 0.43 g, 4.26 mmol) in DCM (25 ml) was stirred at room temperature for 24 h. The reaction mixture was partitioned between DCM (50 ml) and 10% NaHCO3 solution (30 ml). The organic layer was separated, dried over MgSO4 and the solvent removed under vacuum to give a pale yellow solid that was recrystallized from EtOAc/hexane to give the title compound as an off white solid (1.14 g, 81%), δH (CDCl3) 8.46 (1H, dd, J 2.0, 4.7Hz), 8.05 (1H, dd, J 2.0, 7.6Hz), 7.34 (2H, m), 7.25 (2H, m), 7.11 (2H, m), 6.96 (3H, m), 5.24 (2H, s), 5.06 (1H, m), 3.80 (3H, s) and 3.24 (2H, m).

Workup

  1. customThe reaction mixture was partitioned between DCM (50 ml) and 10% NaHCO3 solution (30 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customthe solvent removed under vacuum
  5. customto give a pale yellow solid
  6. customthat was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-31ac82be89bd4e31bc4dfb4d3b80f56b
Source dataset
uspto-grants-2001_12
Patent number
US06329372B1

Reaction notes

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