1-Hydroxybenzotriazole → HCID 68841966, compound

HRID 1889287Notes

Reaction equation

HRID 1889287 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[C:21](O)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[CH3:44][O:45][C:46](=[O:51])[C:47]([NH2:50])([CH3:49])[CH3:48]>CN(C=O)C>[CH3:44][O:45][C:46](=[O:51])[C:47]([CH3:49])([NH:50][C:21]([C:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[CH:10]=[CH:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:22])[CH3:48]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 68840681HCID 68840681, compound

Product 1

HCID 68841966HCID 68841966, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C. to a solution of 165 mg of a mixture of the (E)- and (Z)-isomers of 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid in 2 ml abs. DMF under inert atmosphere 95 mg 1-hydroxybenzotriazole, 110 μl N,N′-diiospropylcarbodiimide and 98 μl N,N-diisopropylethylamine were added. After 15 min at 0° C. 86 mg amino-isobutyric acid methyl ester hydrochloride and 98 μl N,N-diisopropylethylamine were added and the reaction was stirred for 0.5 h at 0° C. and for 4 h at room temperature. Then, the reaction mixture was concentrated, the residue was taken up in ethyl acetate and washed with 2 M HCl, aqueous sat. sodium hydrogen carbonate solution and brine. The organic layer was dried over sodium sulphate, concentrated and purified by chromatography on silica (ethyl acetate/heptane) to yield 85 mg of a mixture of the (E)- and (Z)-isomers of 2-methyl-2-{[1-(4-phenyl-but-1-enyl)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester.

Workup

  1. customAt 0° C.
  2. concentrationThen, the reaction mixture was concentrated
  3. washwashed with 2 M HCl, aqueous sat. sodium hydrogen carbonate solution and brine
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated
  6. custompurified by chromatography on silica (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-d3e11eb8d73047d482054447d0e63880
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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