Hydrochloric Acid → HCID 58124924, compound

HRID 1971684Notes

Reaction equation

HRID 1971684 reaction equation
[CH:1]([N:4]1[C:32](=[O:33])[C:31]2[N:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[C:17]([O:29][CH3:30])[C:18]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])=[CH:19][C:20]=4[C:11]3=[C:10]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[C:9]=2[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C1(OC)C=CC=CC=1.Cl>O1CCOCC1.C([O-])(O)=O.[Na+]>[CH:1]([N:4]1[C:32](=[O:33])[C:31]2[N:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[C:17]([O:29][CH3:30])[C:18]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])=[CH:19][C:20]=4[C:11]3=[C:10]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[C:9]=2[CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 58124886HCID 58124886, compound

Product 1

HCID 58124924HCID 58124924, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of 110 mg of 10o in 1 ml of dioxane, was added 75 μl of anisole and 500 μl of 4N HCl in dioxane. After 1 hr the reaction mixture was diluted with 10 ml of sat. NaHCO3 and the product was extracted with ethyl acetate. The organic layer was washed once with sat. NaCl, dried and concentrated. The residue was triturated with diethyl ether, to provide 90 mg of 10q as white crystalline material. Mp: 250-252° C.; Rf 0.60 (CH2Cl2/methanol 8/2);

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed once with sat. NaCl
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-da3071ef151046169ab0d441d60d0f32
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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