Hydrochloric Acid → HCID 68313163, compound

HRID 2404383Notes

Reaction equation

HRID 2404383 reaction equation
[C:1]1([C@H:7]2[CH2:11][C@@H:10]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([Zn]CC)C.ICI.Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Cl-].[Na+].O.CC(OC)(C)C.C(Cl)Cl>[C:1]1([C@@H:7]2[C@H:8]3[C@H:9]([CH2:16]3)[C@H:10]([NH:12][C:13](=[O:15])[CH3:14])[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 24477Sodium ThiosulfateHCID 68313919HCID 68313919, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 68313163HCID 68313163, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Example 55A (100 mg, 0.497 mmol) and CH2Cl2 (5 mL) was cooled to −10° C. and diethylzinc (1M solution, 4.97 mL, 4.97 mmol) was added at <0° C. After 5 minutes, diiodomethane (0.441 mL, 5.47 mmol) was added at <0° C. The mixture was slowly warmed to ambient temperature and the reaction was complete after 3 hours. The mixture was cooled to <0° C., brine (5 mL) and 2N HCl (5 mL) were added, then diluted with MTBE (50 mL) and added saturated aqueous Na2S2O3 (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (50-100% EtOAc/hexanes, gradient elution) to provide the title compound (82 mg, 0.381 mmol, 77% yield). MS (DCI) M/Z 216 [M+H]+.

Workup

  1. waitthe reaction was complete after 3 hours
  2. temperatureThe mixture was cooled to <0° C.
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (50-100% EtOAc/hexanes, gradient elution)

Sources & evidence

ORD record
ord-688b4443d6ca4e60bf37639cf172472e
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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