Hydrochloric Acid → HCID 71729793, compound

HRID 2280079Notes

Reaction equation

HRID 2280079 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]1[CH2:25][C:17]3([CH2:22][O:21]C(C)(C)[O:19][CH2:18]3)[CH2:16][C:7]1=[C:8]2[C:13](=[O:15])[CH3:14].Cl>C1COCC1>[CH3:26][N:2]([CH3:1])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]1[CH2:25][C:17]([CH2:18][OH:19])([CH2:22][OH:21])[CH2:16][C:7]1=[C:8]2[C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72546103HCID 72546103, compound

Product 1

HCID 71729793HCID 71729793, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried 50 mL one-necked round-bottomed flask was charged with compound 6a (0.036 g, 0.10 mmol) and THF (12 mL). HCl (5 mL of a 1 N aqueous solution) was added and the mixture was stirred at rt for 2 h. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 1:1). The reaction was basified to pH 7 by the dropwise addition of sat'd aq NaHCO3. The layers were separated and the aqueous phase was extracted with ether (3×15 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, gravity filtered, and concentrated under reduced pressure to provide 0.018 g of the title compound as a yellow solid in 57% yield.

Workup

  1. customThe consumption of the starting material
  2. additionThe reaction was basified to pH 7 by the dropwise addition of sat'd aq NaHCO3
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ether (3×15 mL)
  5. washThe combined organic layers were washed with brine (25 mL)
  6. dry with materialdried over MgSO4, gravity
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3fc671de7f574964853f04d16a231cc2
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

Loading…