Hydrochloric Acid → HCID 59737227, compound

HRID 1907766Notes

Reaction equation

HRID 1907766 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[CH:39]=[CH:38][C:13]([C:14]([NH:16][C:17]3[CH:18]=[C:19]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH:20]=[CH:21][C:22]=3[NH:23]C(=O)OC(C)(C)C)=[O:15])=[CH:12][CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].Cl>C(Cl)Cl.O1CCOCC1.CCOC(C)=O>[C:1]([NH:4][C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:16][C:17]3[CH:18]=[C:19]([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[CH:20]=[CH:21][C:22]=3[NH2:23])=[O:15])=[CH:38][CH:39]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59737275HCID 59737275, compound

Product 1

HCID 59737227HCID 59737227, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 407 (0.280 g, 0.526 mmol) in DCM (5 mL) and dioxane (5.0 mL) was added HCl in dioxane (2.4 mL, 9.46 mmol). The mixture was stirred for 3 h at room temperature. The solvent was evaporated and the residue obtained was triturated in Et2O, filtered and dried under vacuum. The light pink solid obtained was suspended in EtOAc, washed with sat NaHCO3, brine, dried over MgSO4, filtered and evaporated to afford a beige solid that was triturated overnight with Et2O. The solid was then filtered and dried under vacuum to give the title compound 408 (167 mg, 69% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue obtained
  3. customwas triturated in Et2O
  4. filtrationfiltered
  5. customdried under vacuum
  6. customThe light pink solid obtained
  7. washwashed
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customto afford a beige solid
  12. customthat was triturated overnight with Et2O
  13. filtrationThe solid was then filtered
  14. customdried under vacuum

Sources & evidence

ORD record
ord-aa7ba7436fde45ef9a1f1d913bfa9ba4
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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