Hydrochloric Acid → HCID 44201312, compound

HRID 1478935Notes

Reaction equation

HRID 1478935 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:12](=[O:29])[C@@H:13]([NH:21]C(=O)OC(C)(C)C)[CH2:14][C:15]3[N:19]([CH3:20])[CH:18]=[N:17][CH:16]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.Cl.C(N(CC)CC)C.[C:42]([CH2:46][C:47](Cl)=[O:48])([CH3:45])([CH3:44])[CH3:43]>ClCCl.O1CCOCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:12](=[O:29])[C@@H:13]([NH:21][C:47](=[O:48])[CH2:46][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:14][C:15]3[N:19]([CH3:20])[CH:18]=[N:17][CH:16]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 44200254HCID 44200254, compound

Product 1

HCID 44201312HCID 44201312, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 17 (320 mg, 0.70 mmol) in dichloromethane (4 ml) was added 4N HCl in dioxane (4 ml). The mixture was stirred for 1 hr at room temperature and concentrated in vacuo. To a solution of the resulting material were added triethylamine (293 μl, 0.49 mmol) and tert-butylacetyl chloride (117 μl, 0.84 mmol). After 30 min, water (10 ml) was added to quench the reaction. The aqueous phase was extracted with dichloromethane (5 ml) and the organic layer was washed with brine (10 ml), dried over anhydrous MgSO4 and concentrated in vacuo. The crude material was purified by preparative TLC (10% MeOH in dichloromethane) to provide compound 69 (220 mg, 70%) as a white solid. [M+H]+ 453.3, HPLC purity: 99%.

Workup

  1. concentrationconcentrated in vacuo
  2. waitAfter 30 min
  3. customto quench
  4. customthe reaction
  5. extractionThe aqueous phase was extracted with dichloromethane (5 ml)
  6. washthe organic layer was washed with brine (10 ml)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by preparative TLC (10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-9059e92ec2964d92b63a785c5ba617c6
Source dataset
uspto-grants-2016_08
Patent number
US09403789B2

Reaction notes

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