1,2-Dichloroethane → HCID 15896052, compound

HRID 1955124Notes

Reaction equation

HRID 1955124 reaction equation
[CH2:1]([N:9]([CH2:20][C:21]([OH:23])=O)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CN1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:46]([O:53][NH2:54])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C=O)C>[CH2:46]([O:53][NH:54][C:21](=[O:23])[CH2:20][N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:11])=[O:12])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-Methylmorpholine2×HCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 15896051HCID 15896051, compound

Product 1

HCID 15896052HCID 15896052, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

[Octyl-(toluene-4-sulfonyl)amino]-acetic acid (4.0 g, 0.012 mol) was taken up in DMF (150 ml) and treated at room temperature with NMM (1.55 ml, 0.014 mol) followed by EDC (2.92 g, 0.015 mol). The reaction mixture was allowed to stir for 15 minutes at room temperature before the addition of HOBt (2.1 g, 0.016 mol). The reaction mixture was left to stir for a further 20 minutes before a mixture of O-benzylhydroxylamine hydrochloride (1.87 g, 0.012 mol) and NMM (2.6 ml, 0.024 mol) in DMF (50 ml) was added. The reaction mixture was allowed to stir at room temperature for a further 48 h. The DMF was removed under reduced pressure and the resulting crude oil was dissolved in ethyl acetate (200 ml). The solution was washed consecutively with 1M HCl, 0.5M Na2CO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography (silica gel, 10% methanol in dichloromethane) to give an oil which was further purified by flash chromatography (silica gel, 20% ethyl acetate in hexane) to give the title compound as a white solid (1.91 g, 37%). 1H NMR: δ (CDCl3), 9.39 (1 H, br s), 7.65 (2H, d, J=8.2 Hz), 7.45-7.20 (7H, m), 4.91 (2H, s), 3.67 (2H, br s), 3.07 (2H, dd, J=7.5, 7.9 Hz), 2.40 (3H, s), 1.50-1.33 (2H, m), 1.31-1.10 (10H, m) and 0.86 (3H, t, J=6.5 Hz).

Workup

  1. waitThe reaction mixture was left
  2. additionwas added
  3. customThe DMF was removed under reduced pressure
  4. dissolutionthe resulting crude oil was dissolved in ethyl acetate (200 ml)
  5. washThe solution was washed consecutively with 1M HCl, 0.5M Na2CO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude oil was purified by flash chromatography (silica gel, 10% methanol in dichloromethane)
  10. customto give an oil which
  11. customwas further purified by flash chromatography (silica gel, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-31b6b64c3729472ead595164cb43dad0
Source dataset
uspto-grants-2000_09
Patent number
US06124332

Reaction notes

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