HCID 67793061, compound → HCID 67793361, compound

HRID 1034242Notes

Reaction equation

HRID 1034242 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C@H:13]2[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][C@H:14]2[C:24]([O:26]C(C)(C)C)=[O:25])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C@H:13]2[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][C@H:14]2[C:24]([OH:26])=[O:25])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 67793061HCID 67793061, compound

Product 1

HCID 67793361HCID 67793361, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The tert-butyl ester of Example 10 (160 mg, 0.35 mmol) was dissolved in 5ml of trifluoroacetic acid and stirred for 16 h at room temperature after which time the reaction was concentrated in vacuo. The resulting material was radially chromatographed on silica gel eluting with EtOH/CH2Cl2 /HOAc (5/95/1) to give the title compound (119 mg, 85%) as a colorless solid. DSC=139.0°-143° C. @5.7 J/g and 191.7°- 203.5° [email protected] J/g. MS M+1 calcd for C17H21N3O4Cl2 403, found 403.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe resulting material was radially chromatographed on silica gel eluting with EtOH/CH2Cl2 /HOAc (5/95/1)

Sources & evidence

ORD record
ord-5aaba9fde643463b960f86d178fa12a1
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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