O-methyl-L-tyrosine N-Methylamide → 6-Methyl-4-[[[1-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]carbonyl]hept-3-enoic acid, methyl ester

HRID 1031247Notes

Reaction equation

HRID 1031247 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH:6]=[C:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=O)=[O:4].[CH3:15][NH:16][C:17](=[O:29])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[NH2:19]>ClCCl>[CH3:13][CH:12]([CH3:14])[CH2:11][C:7]([C:8]([NH:19][CH:18]([C:17]([NH:16][CH3:15])=[O:29])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)=[O:10])=[CH:6][CH2:5][C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 14303038O-methyl-L-tyrosine N-MethylamideHCID 538598124-Methoxycarbonyl-2-(2-methylpropyl)but-2-enoic acid

Product 1

HCID 851152346-Methyl-4-[[[1-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]carbonyl]hept-3-enoic acid, methyl esterYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Dicyclohexylcarbodiimide (515 mg, 2.5 mmol) was added to an ice-cooled solution of 4-methoxycarbonyl-2-(2-methylpropyl)but-2-enoic acid (500 mg, 2.5 mmol) and O-methyl-L-tyrosine N-methylamide (520 mg, 2.5 mmol) in dry dichloromethane (30 ml), and the mixture was stirred at room temperature for 18 h. The precipitated solid was filtered off and washed with a little dichloromethane, then the organic solution was washed successively with 1 N hydrochloric acid (20 ml), 1 N sodium bicarbonate (20 ml), and water. The solution was dried (MgSO4) and evaporated in vacuo. Column chromatography (30 g silica) of the residual solid, eluting with 5% methanol/dichloromethane gave the title compound (520 mg, 53%), m.p. 142°-144° C. (dichloromethane/pentane).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with a little dichloromethane
  3. washthe organic solution was washed successively with 1 N hydrochloric acid (20 ml), 1 N sodium bicarbonate (20 ml), and water
  4. dry with materialThe solution was dried (MgSO4)
  5. customevaporated in vacuo
  6. washColumn chromatography (30 g silica) of the residual solid, eluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-9850084518aa4b078e4f5093254fa10a
Source dataset
uspto-grants-1992_04
Patent number
US05109000

Reaction notes

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