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 2108276Notes

Reaction equation

HRID 2108276 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 1N hydrochloric acid (20 ml), 1N 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 1N hydrochloric acid (20 ml), 1N 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-5df8e4a4564241689f6433ba7df44eee
Source dataset
uspto-grants-1990_06
Patent number
US04937243

Reaction notes

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