Sulfuric Acid → HCID 131727390, compound

HRID 2109141Notes

Reaction equation

HRID 2109141 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C@H:18]([OH:34])[CH2:19][NH:20][C:21]([CH3:33])([CH3:32])[CH2:22][CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24]2)[CH:12]=[CH:11][C:10]=1[CH:35]([CH2:39][CH:40]=[CH2:41])[C:36]([OH:38])=[O:37].S(=O)(=O)(O)O>C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:2]([O:37][C:36](=[O:38])[CH:35]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][C@H:18]([OH:34])[CH2:19][NH:20][C:21]([CH3:33])([CH3:32])[CH2:22][CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24]2)=[C:14]([Cl:15])[C:9]=1[Cl:8])[CH2:39][CH:40]=[CH2:41])[CH3:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 131727392HCID 131727392, compound

Product 1

HCID 131727390HCID 131727390, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The acid of Example 19 (0.5 g) was dissolved in absolute ethanol (10 mL) and catalytic amount of conc.sulfuric acid was added. The reaction was stirred and heated to reflux overnight. Next day the reaction was concentrated and diluted with ethyl acetate and washed with 2.5N NaOH (2×20 mL), brine (20 mL) and dried over sodium sulfate. The crude mixture was purified by HPLC (eluted with CH3CN/H2O containing 0.1% TFA) to produce the desired product in 81% yield (0.43 g). MS(ES) m/e 536 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) : 8.35-8.48 (brs, 2H), 7.31-7.10 (m, 6H), 4.17-4.01 (m, 5H), 3.26-3.05 (m, 4H), 2.69-2.50 (m, 7H), 2.32 (t, 2H), 1.94 (d, 2H), 1.58-1.54 (t, 2H), 1.33 (s, 3H), 1.35 (s, 3H), 1.18 (t, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationNext day the reaction was concentrated
  4. additiondiluted with ethyl acetate
  5. washwashed with 2.5N NaOH (2×20 mL), brine (20 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe crude mixture was purified by HPLC (eluted with CH3CN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-745e1b5e5d9444b7aa8a15fa11470cc0
Source dataset
uspto-grants-2009_04
Patent number
US07514473B2

Reaction notes

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