Triethylamine → [4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester

HRID 2121235Notes

Reaction equation

HRID 2121235 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:5]=1)([O-:3])=[O:2].C1C=C2C(N(O)N=NC2=CC=1)=O.Cl.[CH3:33][O:34][C:35](=[O:42])[C@H:36]([CH2:38][CH2:39][S:40][CH3:41])[NH2:37].CCN=C=NCCCN(C)C.CCN(CC)CC>CN(C=O)C.C(OCC)(=O)C>[CH3:33][O:34][C:35](=[O:42])[C@H:36]([CH2:38][CH2:39][S:40][CH3:41])[NH:37][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 234360742-(2-Methylphenyl)-4-nitrobenzoic acid

Product 1

HCID 53719134[4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl esterYield 99.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 308A (604 mg, 2.35 mmol) and HOOBT (574 mg, 3.52 mmol) were dissolved in DMF (10 mL) and methionine methyl ester HCl (679 mg, 3.52 mmol) and EDCI (676 mg, 3.52 mmol) were added followed by Et3N (476 mg, 0.65 mL, 4.7 mmol). The reaction was stirred for 12 hours and then was taken up in ethyl acetate and washed successively with brine (3×) and water (3×). The ethyl acetate layer was dried over Na2SO4, filtered and evaporated. Purification by chromatography on silica gel (5% methanol-ethyl acetate) gave the desired compound (940 mg, 98%).

Workup

  1. washwashed successively with brine (3×) and water (3×)
  2. dry with materialThe ethyl acetate layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography on silica gel (5% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-0aa2890e021e459dbc184aa991d60333
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…