1-Hydroxybenzotriazole → 2-Methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester

HRID 1889268Notes

Reaction equation

HRID 1889268 reaction equation
[CH3:1][CH:2]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22](O)=[O:23])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.Cl.[CH3:57][O:58][C:59](=[O:64])[C:60]([NH2:63])([CH3:62])[CH3:61]>CN(C=O)C>[CH3:57][O:58][C:59](=[O:64])[C:60]([CH3:62])([NH:63][C:22]([C:13]1[CH:14]=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]=1[O:11][CH:2]([CH3:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:23])[CH3:61]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 68842959(1-Methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid

Product 1

HCID 688437262-Methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg—(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid in 1.5 ml abs. DMF under inert atmosphere 45 mg 1-hydroxybenzotriazole, 83 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 70 μl of N,N-diisopropylethylamine were added at 0° C. After 30 minutes at 0° C. 36 mg of 2-aminoisobutyric acid methyl ester hydrochloride, followed by 70 μl of N,N-diisopropylethylamine were added. After 16 h at room temperature the reaction mixture was concentrated, the residue was taken up in ethyl acetate and washed with 2 M HCl, aqueous sodium carbonate solution (10%) and brine. The organic layer was dried over magnesium sulphate, and concentrated to yield 114 mg of 2-methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester.

Workup

  1. additionwere added
  2. concentrationAfter 16 h at room temperature the reaction mixture was concentrated
  3. washwashed with 2 M HCl, aqueous sodium carbonate solution (10%) and brine
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1078dcb52c5c4c2fa369cbce2f772ff6
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

Loading…