Water → HCID 131720362, compound

HRID 1940484Notes

Reaction equation

HRID 1940484 reaction equation
[CH:1]12[CH2:6][CH:5]1[CH2:4][NH:3][CH:2]2[C:7]([NH:9][C:10]1[C:11]([F:24])=[CH:12][C:13]([Cl:23])=[C:14]([CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=1)=[O:8].C(N(CC)CC)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)Cl>[Cl:23][C:13]1[CH:12]=[C:11]([F:24])[C:10]([N:9]2[C:7](=[O:8])[CH:2]3[CH:1]4[CH2:6][CH:5]4[CH2:4][N:3]3[C:33]2=[O:35])=[CH:15][C:14]=1[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 131720363HCID 131720363, compound

Product 1

HCID 131720362HCID 131720362, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of the compound of Step G, Example 2, (300.0 mg, 0.85 mmol) and triethylamine (1.18 mL, 8.5 mmol) in CH2Cl2 (50 mL), under N2, at room temperature, was added dropwise a solution of triphosgene (84.0 mg, 0.28 mmol) in CH2Cl2 (10 mL) over a period of 15 minutes. The solution was stirred at room temperature for 10 minutes. A mixture of CH2Cl2 (100 mL) and H2O (50 mL) was added. The organic layer was separated, dried over MgSO4 and concentrated under reduced pressure to dryness. The residue was chromatographed on silica gel using 25% ethyl acetate in hexane as eluent. Fractions containing the title compound were combined and evaporated under reduce pressure to yield the title compound, a compound of the invention, as a white solid (84.0 mg), 26%; m.p. 154°-156° C., IR (nujol, cm-1): 1720.4 (C=O); 1H NMR δ: 0.61-0.63 (q,1H), 1.32-1.36 (m,4H), 2.01-2.03 (m,1H), 2.11-2.18 (m,1H), 3.12-3.18 (d,1H), 4.18-4.28 (m,4H), 6.37-6.41 (d,1H), 7.32-7.35 (d,1H), 7.59-7.62 (d,1H), 7.94-7.99 (d,1H).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue was chromatographed on silica gel using 25% ethyl acetate in hexane as eluent
  6. additionFractions containing the title compound
  7. customevaporated

Sources & evidence

ORD record
ord-92779a962e634d91bf80d33ffc7bee5d
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

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