Triethylamine → HCID 18758447, compound

HRID 433810Notes

Reaction equation

HRID 433810 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].C(N(CC)CC)C.C([O:16][C:17](=[O:31])[C:18](=O)[CH2:19][S:20][C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1)C>C(Cl)Cl.CO>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[S:20][C:19]1[CH:18]([C:17]([OH:31])=[O:16])[O:5][C:2](=[O:6])[C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 15620607Glyoxylic acid, monohydrateHCID 67300216Ethyl 3-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxopropanoate

Product 1

HCID 18758447HCID 18758447, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

To a solution of glyoxylic acid monohydrate (98 mg, 1.03 mmol) in 6 mL methylenechloride/methanol (5:1) was added triethylamine (418 μL, 3.0 mmol) and stirred viogorously. 3-(benzothiazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (281 mg, 1.06 mmol) in 6 mL methylenechloride/methanol (5:1) was added dropwise over a period of 3 hours and the reaction was stirred overnight (15 hrs) at room temperature. The reaction mixture was then neutralized with NaH2PO4 and washed with ethylacetate. The resulting very polar product remained in the aqueous layer and was purified by reverse-phase HPLC. The pure fractions were pooled and concentrated under reduced pressure. Upon evaporation of solvent, 3-(benzothiazol-2-ylsulfanyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-2-carboxylic acid precipitated out (70 mg) as a white solid which was filtered and washed with water. The filtrate was collected and lyophilized to afford a pale yellow solid which was determined to be the triethylamine salt of the desired product. 1H-NMR (MeOD, 300 MHz) δ (ppm): 7.92-7.87 (m, 2H), 7.51-7.38 (m, 2H), 5.68 (s, 1H). MS (ESI) m/z: 310 (M+H+).

Workup

  1. stirringthe reaction was stirred overnight (15 hrs) at room temperature
  2. washwashed with ethylacetate
  3. customwas purified by reverse-phase HPLC
  4. concentrationconcentrated under reduced pressure
  5. customUpon evaporation of solvent, 3-(benzothiazol-2-ylsulfanyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-2-carboxylic acid
  6. customprecipitated out (70 mg) as a white solid which
  7. filtrationwas filtered
  8. washwashed with water
  9. customThe filtrate was collected
  10. customto afford a pale yellow solid which

Sources & evidence

ORD record
ord-fdb3dfd101844954bcd077e6a5bca80f
Source dataset
uspto-grants-2003_12
Patent number
US06667330B2

Reaction notes

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