Hydrochloric Acid → HCID 72546335, compound

HRID 2280081Notes

Reaction equation

HRID 2280081 reaction equation
CC1(C)[O:7][CH2:6][C:5]2([CH2:27][C:10]3=[C:11]([C:24](=[O:26])[CH3:25])[C:12]4[C:17]([CH:18]=[C:9]3[CH2:8]2)=[C:16]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:15]=[CH:14][CH:13]=4)[CH2:4][O:3]1.Cl>C1COCC1>[OH:3][CH2:4][C:5]1([CH2:6][OH:7])[CH2:8][C:9]2=[CH:18][C:17]3[C:12]([C:11]([C:24](=[O:26])[CH3:25])=[C:10]2[CH2:27]1)=[CH:13][CH:14]=[CH:15][C:16]=3[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86702748HCID 86702748, compound

Product 1

HCID 72546335HCID 72546335, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried 50 mL one-necked round-bottomed flask was charged with compound 6d (0.013 g, 0.034 mmol) and THF (10 mL). HCl (3 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 0.006 g of the title compound as a yellow solid in 52% 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-f859f04532aa4a4cbd4e10ee6f1cbe53
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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