Sulfuric Acid → HCID 131727390, compound

HRID 1171179Notes

Reaction equation

HRID 1171179 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-194eea1275d4484dbe01fc1a99232b5e
Source dataset
uspto-grants-2010_11
Patent number
US07829594B2

Reaction notes

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