Triethylamine → HCID 11561276, compound

HRID 1815486Notes

Reaction equation

HRID 1815486 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]3)=[O:20])=[CH:13][C:12]=2[N+:30]([O-:32])=[O:31])[CH:7]=[CH:8][CH:9]=1)(O)=[O:2].CCN(CC)CC.ClC(OCC)=O>C1COCC1>[OH:2][CH2:1][C:4]1[CH:5]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([N:21]3[CH2:22][CH2:23][N:24]([C:27](=[O:29])[CH3:28])[CH2:25][CH2:26]3)=[O:20])=[CH:13][C:12]=2[N+:30]([O-:32])=[O:31])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86592886HCID 86592886, compound

Product 1

HCID 11561276HCID 11561276, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of benzoic acid from Example 92A (255 mg, 0.56 mmol) in 5 mL of anhydrous THF at 0° C. was added in turn Et3N (102 mL, 0.73 mmol) and ethyl chloroformate (70 mL, 0.73 mmol). After 60 minutes, the reaction mixture was filtered through celite plug into a stirred solution of NaBH4 in water at 0° C. The resulting reaction mixture stirred at 0° C. for 2 hours before it was extracted with EtOAc (2×20 mL). The combined organic layers were washed with 3N HCl, brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The crude product was purified using Gilson Preparative HPLC as described in Example 38B to give the title compound (80 mg, 32% yield) as a light-yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 2.04 (s, 3H), 3.40-3.79 (m, 8H), 4.56 (s, 2H), 5.38 (br s, 1H), 6.85 (d, J=8.7 Hz, 1H), 7.42 (d, J=15.6 Hz, 1H), 7.52 (br s, 3H), 7.57 (br s, 2H), 7.91 (dd, J=2.1, 8.7 Hz, 1H), 8.66 (d, J=2.1 Hz, 1H). MS (APCI+) (M+NH4)+ at m/z 459.

Workup

  1. filtrationthe reaction mixture was filtered through celite plug into a stirred solution of NaBH4 in water at 0° C
  2. customThe resulting reaction mixture
  3. extractionwas extracted with EtOAc (2×20 mL)
  4. washThe combined organic layers were washed with 3N HCl, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-9c699ba9d4fd484e835c05385002dea1
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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