HCID 117599097, compound → HCID 117598982, compound

HRID 522363Notes

Reaction equation

HRID 522363 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C@@H:12]2[CH2:16][N:15](C(OC(C)(C)C)=O)[C@H:14]([C:24](=[O:36])[NH:25][C@:26]3([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:28][C@H:27]3[CH:29]=[CH2:30])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C@@H:12]2[CH2:16][NH:15][C@H:14]([C:24]([NH:25][C@:26]3([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:28][C@H:27]3[CH:29]=[CH2:30])=[O:36])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 117599097HCID 117599097, compound

Product 1

HCID 117598982HCID 117598982, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

HCl (4M in dioxane, 300 ml) was added to the product of Step 2 (40 g) and the solution was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and a saturated sodium bicarbonate solution was added. The phases were separated. The precipitated solid was filtrated from the organic layer to give the desired product (33.8 g) as a white solid. LRMS (ES+) m/z 487.0 (M+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. additiona saturated sodium bicarbonate solution was added
  4. customThe phases were separated
  5. filtrationThe precipitated solid was filtrated from the organic layer

Sources & evidence

ORD record
ord-938e6d3dd8854c89b9f4300621eb2df1
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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