HCID 54210476, compound → HCID 69892945, compound

HRID 2121226Notes

Reaction equation

HRID 2121226 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]2[CH:25]=[CH:24][C:12]([C:13]([NH:15][C@H:16]([C:21]([OH:23])=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=O)=[C:11]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH:10]=2)[CH:2]=1>C(O)CCC.OS(O)(=O)=O>[CH2:2]([O:23][C:21](=[O:22])[C@H:16]([CH2:17][CH2:18][S:19][CH3:20])[NH:15][CH2:13][C:12]1[CH:24]=[CH:25][C:9]([CH:8]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:10][C:11]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 54210476HCID 54210476, compound

Product 1

HCID 69892945HCID 69892945, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 2631-ButanolSolvent

Procedure

{4-[2-(pyrid-3-yl)ethenyl]-2-(2-methylphenyl)benzoyl}methionine (138 mg, 0.30 mmol) was heated at 100° C. for 2 hours in n-butanol (5 mL) with 1 drop of H2SO4. The reaction was evaporated to dryness, partitioned between ethyl acetate and 5% NaHCO3, washed with water and brine, and dried over Na2SO4 to provide the title compound in 86% yield. 1H NMR (CDCl3, 300 MHz) δ 0.92 (t, 3H), 1.35 (m, 2H), 1.60 (m, 2H), 1.86 (m, 1H), 2.1 (m, 9H), 4.08 (m, 2H), 4.62 (m, 1H), 5.97 (d, 1H), 7.18-8.04 (m, 1H), 8.53 (s, 1H), 8.77 (s, 1H). MS m/e 503 (M+H)+.

Workup

  1. customThe reaction was evaporated to dryness
  2. custompartitioned between ethyl acetate and 5% NaHCO3
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-52482e97972142c4bc25c7c94adbe4f6
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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