HCID 57635103, compound → HCID 57635098, compound

HRID 535956Notes

Reaction equation

HRID 535956 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]2[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][C:2]([CH3:35])([CH3:34])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:14]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 57635103HCID 57635103, compound

Product 1

HCID 57635098HCID 57635098, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Compound 312 (0.48 g) in DCM (5 mL) and TFA (5 mL) was stirred at room temperature for thirty minutes. The solvents were removed by evaporation under reduced pressure and the residue was extracted between saturated aqueous NaHCO3 and EtOAc. The aqueous phase was saturated with sodium chloride and extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure to give Compound 314 (0.38 g).

Workup

  1. customThe solvents were removed by evaporation under reduced pressure
  2. extractionthe residue was extracted between saturated aqueous NaHCO3 and EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-96f6f042702549f3ba3279ec8d9f1825
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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