1,2-Dichloroethane → acetic acid 4-[-(benzylsulfanylcarbonylmethyl-carbamoyl)-methyl]-2-oxo-2H-chromen-7-yl ester

HRID 270533Notes

Reaction equation

HRID 270533 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH2:16][C:17]([OH:19])=O)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:34]([S:41][C:42](=[O:45])[CH2:43][NH2:44])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1.CN(C=O)C>[CH2:34]([S:41][C:42]([CH2:43][NH:44][C:17]([CH2:16][C:9]1[C:8]2[C:13](=[CH:14][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)[O:12][C:11](=[O:15])[CH:10]=1)=[O:19])=[O:45])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 12514017(7-Acetoxy-2-oxo-2H-chromen-4-yl)-acetic acidHCID 86206484S-benzyl 2-aminoethanethioate

Product 1

HCID 86760755acetic acid 4-[-(benzylsulfanylcarbonylmethyl-carbamoyl)-methyl]-2-oxo-2H-chromen-7-yl esterYield 56.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 (0.162 g, 0.62 mmol) in dry THF was added EDC (0.13 g, 0.68 mmol) and HOBt (0.104 g, 0.68 mmol). The reaction was stirred for 30 minutes under ice-cold conditions, followed by addition of 8 (0.135 g, 0.62 mmol) dissolved in minimal amount of DMF. The resulting solution was stirred further for 6 hours at RT. Upon removal of the solvent in vacuo, the resulting mixture was taken into ethyl acetate and washed with 1 N HCl (2×30 ml), water (2×30 ml) and brine (2×30 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to afford a white solid, which was further purified by flash chromatography (silica gel, dichloromethane/ethanol=9:1) to afford 1 (0.15 g, 56%). 1H NMR (300 MHz, CDCl3) δ 7.67 (d, J=9.0 Hz, 1H), 7.27-7.23 (m, 7H), 6.38 (s, 1H), 4.1 (s, 2H), 3.73 (s, 2H), 2.91 (s, 2H), 2.32 (s, 3H). MS (ESI): m/z 448.0 [(M+Na)]+.

Workup

  1. stirringThe resulting solution was stirred further for 6 hours at RT
  2. customUpon removal of the solvent in vacuo
  3. washwashed with 1 N HCl (2×30 ml), water (2×30 ml) and brine (2×30 ml)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford a white solid, which
  7. customwas further purified by flash chromatography (silica gel, dichloromethane/ethanol=9:1)

Sources & evidence

ORD record
ord-a3634aac335441ff88abcfb5fa2c2ec3
Source dataset
uspto-grants-2008_11
Patent number
US07449558B2

Reaction notes

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