HCID 67795095, compound → HCID 67795010, compound

HRID 1034240Notes

Reaction equation

HRID 1034240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([NH:11][C@H:12]2[C:16](=[O:17])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][C@H:13]2[C:23]([O:25]C(C)(C)C)=[O:24])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([NH:11][C@H:12]2[C:16](=[O:17])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][C@H:13]2[C:23]([OH:25])=[O:24])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 67795095HCID 67795095, compound

Product 1

HCID 67795010HCID 67795010, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The tert-butyl ester of Example 9 (145 mg, 0.327 mmol) was dissolved in 5 ml 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 (89 mg, 77%) as a colorless solid. Anal calcd for C17H20N2O4Cl2 : C, 52.73; H, 5.20; N, 7.23. Found: C, 52.43; H, 5.32; N, 7.02. DSC=204.6°-210.2° [email protected] J/g. MS M+1 calcd for C17H20N2O4Cl2 387, found 387.

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-97f8bf592e1c42868bd8f379464da413
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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