HCID 67794946, compound → HCID 67793641, compound

HRID 1034238Notes

Reaction equation

HRID 1034238 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C@H:13]1[C:17](=[O:18])[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][C@H:14]1[C:25]([O:27]C(C)(C)C)=[O:26])=[O:11]>FC(F)(F)C(O)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C@H:13]1[C:17](=[O:18])[N:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:15][C@H:14]1[C:25]([OH:27])=[O:26])=[O:11]

Participants

3

Reactant 1

HCID 67794946HCID 67794946, compound

Product 1

HCID 67793641HCID 67793641, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The tert-butyl ester of Example 5 (110 mg, 0.26 mmol) was dissolved in 3 ml of trifluoroacetic acid and the resulting solution was stirred for 2 days at room temperature. Concentration in vacuo gave an oil which was chromatographed on silica gel eluting with 5/91/1 EtOH/CH2Cl2 /HOAc to give the title compound (41 mg, 43%) as a colorless solid. MS calcd C20H17N3O4 363, found 363. DSC=214.2°-229.3° C. @48.7 J/g.

Workup

  1. concentrationConcentration in vacuo
  2. customgave an oil which
  3. customwas chromatographed on silica gel eluting with 5/91/1 EtOH/CH2Cl2 /HOAc

Sources & evidence

ORD record
ord-bce415e80aeb4ab9934668f18e714165
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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