HCID 67794289, compound → HCID 67821704, compound

HRID 1034244Notes

Reaction equation

HRID 1034244 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C@H:11]([NH:14][C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[O:16])[C@H:10]([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:9]1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C@H:11]([NH:14][C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[O:16])[C@H:10]([C:27]([OH:29])=[O:28])[CH2:9]1

Participants

3

Reactant 1

HCID 67794289HCID 67794289, compound

Product 1

HCID 67821704HCID 67821704, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The tert-butyl ester of Example 20 (388 mg, 0.865 mmol) was dissolved in 3 ml of trifluoroacetic acid and stirred for 18 h at room temperature. Concentration in vacuo gave a solid which was chromatographed on a silica gel chromatotron plate (4 mm) eluting with 3/1/96 EtOH/CH2Cl2 /HOAc to give the title compound (183 mg, 54%) as a solid. Anal calcd for C22H17N2O4F. H2O: C, 66.40; H, 4.67; N, 6.83. Found C, 64.55; H, 4.42; N, 6.71. MS calcd for C22H17N2O4F 392, found 392. DSC=182.9°-185.2° [email protected] J/g.

Workup

  1. concentrationConcentration in vacuo
  2. customgave a solid which
  3. customwas chromatographed on a silica gel chromatotron plate (4 mm)
  4. washeluting with 3/1/96 EtOH/CH2Cl2 /HOAc

Sources & evidence

ORD record
ord-07433b1522604a3fba4012f7a7789697
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

Loading…