Triethylamine → HCID 9796787, compound

HRID 1062362Notes

Reaction equation

HRID 1062362 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=2)[O:15][CH2:16][C:17](O)=[O:18])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.[NH2:39][OH:40].C[O-].[Na+]>O1CCCC1>[OH:40][NH:39][C:17](=[O:18])[CH2:16][O:15][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])/[CH:8]=[CH:7]/[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 69730921HCID 69730921, compound

Product 1

HCID 9796787HCID 9796787, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(3-phenyl-acryloylamino)-phenoxy]-acetic acid (9) (0.297 g, 1.0 mmol) in tetrahydrofuran (3 ml) at 0÷5° C. temperature (ice bath) triethylamine (0.18 ml, 1.3 mmol) followed by iso-butyl chloroformate (0.15 ml, 1.15 mmol) were added. The reaction mixture was stirred for 20 min. In another vessel, a mixture of hydroxylamine hydrochloride (0.122 g, 1.7 mmol) and sodium methoxide (0.095 mg, 1.75 mmol) was prepared. The both mixtures were combined and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate (20 ml) and the organic layer was washed successively with 1N KH2PO4, water, brine, and dried (Na2SO4). The solvent was partially removed until the formation of a precipitate started. The mixture was allowed to stand at room temperature for 6 hours. The precipitate was filtered and washed with diethyl ether to give the title compound (0.090 g, 30%). M.p. 163° C. (dec.). 1H NMR (DMSO-d6, HMDSO), δ: 4.45 (s, 2H); 6.60-6.73 (m, 1H); 6.83 (d, 1H, J=15.6 Hz); 7.18-7.30 (m, 2H); 7.36-7.51 (m, 4H); 7.53-7.68 (m, 3H); 8.98 (s, 1H); 10.23 (s,1H); 10.87 (s, 1H). HPLC analysis on Zorbax SB-C18 column: impurities ˜1% (column size 4.6×150 mm; mobile phase acetonitrile—0.1% H3PO4, gradient from 50:50 to 100:0; detector UV 270 nm; sample concentration 0.7 mg/ml, flow rate 1.0 ml/min). Anal. Calcd for C17H16N2O4: C, 65.38; H, 5.16, N 8.97. Found: C, 65.09, H, 5.14, N, 8.73.

Workup

  1. additionwere added
  2. customwas prepared
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. extractionThe reaction mixture was extracted with ethyl acetate (20 ml)
  5. washthe organic layer was washed successively with 1N KH2PO4, water, brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was partially removed until the formation of a precipitate
  8. waitto stand at room temperature for 6 hours
  9. filtrationThe precipitate was filtered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1133b71d26a647ed82230b0eff6c5e8b
Source dataset
uspto-grants-2005_11
Patent number
US06960685B2

Reaction notes

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