HCID 58777638, compound → HCID 21070477, compound

HRID 1371776Notes

Reaction equation

HRID 1371776 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[N:18]=[C:17]([NH2:19])[C:16]([C:20](=[O:31])[C:21]3[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[C:23]([F:29])[C:22]=3[F:30])=[CH:15][N:14]=2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:19][C:17]1[C:16]([C:20]([C:21]2[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[C:23]([F:29])[C:22]=2[F:30])=[O:31])=[CH:15][N:14]=[C:13]([NH:12][CH:10]2[CH2:11][NH:8][CH2:9]2)[N:18]=1

Participants

4

Reactant 1

HCID 58777638HCID 58777638, compound

Product 1

HCID 21070477HCID 21070477, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred suspension of the protected amine (940 mg, 2.16 mmol, Example 319) in methylene chloride (30 mL), trifluoroacetic acid (20 mL) was added at 0° C. and the mixture stirred for 2 hours. The solvent was removed and the residue was partitioned between ethyl acetate and 5% sodium carbonate solution. The aqueous layer was extracted with ethyl acetate/tetrahydrofuran (1:1, 3×10 ml). The extracts were combined and the solution was dried with sodium sulfate. Removal of solvent gave a yellow solid. 711 mg, 98%. MS (ES) MH+=336.

Workup

  1. additionwas added at 0° C.
  2. customThe solvent was removed
  3. customthe residue was partitioned between ethyl acetate and 5% sodium carbonate solution
  4. extractionThe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (1:1, 3×10 ml)
  5. dry with materialthe solution was dried with sodium sulfate
  6. customRemoval of solvent
  7. customgave a yellow solid

Sources & evidence

ORD record
ord-950f9a34361947de9ab1880394d92c8d
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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