Hydrochloric Acid → HCID 58124942, compound

HRID 1971733Notes

Reaction equation

HRID 1971733 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:31])[C:18]([N:20]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[CH:26])=[O:19])[CH:9]2[C:12]([O:14]CC)=[O:13])=[CH:4][C:3]=1[O:32][CH3:33].[OH-].[K+].Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:31])[C:18]([N:20]([C:27]([CH3:29])([CH3:30])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[CH:26])=[O:19])[CH:9]2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:32][CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58124910HCID 58124910, compound

Product 1

HCID 58124942HCID 58124942, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 480 mg of 19b in 10 ml of dioxane was mixed with 200 mg of KOH in 2 ml of water. The mixture was stirred at rt for 3 h and then diluted with 40 ml of water and acidified to pH 3 with 0.5 N HCl. The product was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated, to provide 420 mg of 19c as white amorphous material; MS-ESI: [M+1] 495.19 and 493.18. NMR (CDCl3) δ 1.43 (m, 2, CH2), 1.53 (s, 9, tertC4H9), 1.68-1.90 (bm, 2, CH2), 1.92 (t, 1, CH), 2.16 (m, 2, CH2), 2.80-3.00 (bm, 2, CH2), 3.22-3.45 (bm, 2, CH2), 3.68 (m, 2, CH2), 3.88 (s, 3, OCH3), 5.74 (s, 1, CH), 6.65 (s, 1, ArH), 7.73 (s, 1, ArH).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c04f7ffc83df4ad39664e9ed1e6b5dc9
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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