Hydrochloric Acid → HCID 72546334, compound

HRID 2280080Notes

Reaction equation

HRID 2280080 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]1[CH2:28][C:20]3([CH2:25][O:24]C(C)(C)[O:22][CH2:21]3)[CH2:19][C:7]1=[C:8]2[C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].Cl>C1COCC1>[CH3:29][N:2]([CH3:1])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]1[CH2:28][C:20]([CH2:21][OH:22])([CH2:25][OH:24])[CH2:19][C:7]1=[C:8]2[C:13](=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72546104HCID 72546104, compound

Product 1

HCID 72546334HCID 72546334, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried 25 mL one-necked round-bottomed flask was charged with compound 6b (0.014 g, 0.035 mmol) and THF (5 mL). HCl (2 mL of a 1 N aqueous solution) was added and the mixture was stirred at rt for 1 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 0.012 g of the title compound as a yellow solid in 96% 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-8fb83c990d3c47d8bc11384dc7001ba8
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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