Ammonium Acetate → HCID 18626421, compound

HRID 2303341Notes

Reaction equation

HRID 2303341 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=O)[CH2:18][CH:19]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:40]>C(O)(=O)C.C(OCC)(=O)C>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[NH:40][C:17]([CH:14]3[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12][CH2:13]3)=[CH:18][C:19]=2[C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 18626427HCID 18626427, compound

Product 1

HCID 18626421HCID 18626421, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 2 was heated in 5 ml of acetic acid in the presence of 2.0 g ammonium acetate at 110° C. for 1.5 hours. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with water. The combined organic phases were washed with brine and dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by MPLC over silica gel eluting with 2% MeOH/CH2Cl2 to give the desired product. H1-NMR (CDCl3, 300 MHz):1.67 (m, 2H); 2.02 (bd, 2h); 2.75-3.0 (m, 3H); 4.29 bd, 2H); 5.12 (s, 2H); 6.19 (d, 1H); 7.03 (t, 2H); 7.18 (dd, 2H); 7.25-7.39 (m, 6H); 8.39 (dd, 2H); 8.52 (bs, 1H). FAB ms: C28H26N3O2F:455; Observed: 456 (M++1).

Workup

  1. washwashed with water
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by MPLC over silica gel eluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-8d121d7b3bdd4e24aabb72e2b000fc55
Source dataset
uspto-grants-2002_08
Patent number
US06432980B1

Reaction notes

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