HCID 58677537, compound → HCID 58677644, compound

HRID 1012651Notes

Reaction equation

HRID 1012651 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH:26]3[CH2:30][O:29]C(C)(C)[O:27]3)[CH:21]=[CH:20][C:19]=2[CH3:33])=[O:17])=[C:12]([N+:34]([O-:36])=[O:35])[CH:11]=1>C(O)(C(F)(F)F)=O.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH:26]([OH:27])[CH2:30][OH:29])[CH:21]=[CH:20][C:19]=2[CH3:33])=[O:17])=[C:12]([N+:34]([O-:36])=[O:35])[CH:11]=1

Participants

3

Reactant 1

HCID 58677537HCID 58677537, compound

Product 1

HCID 58677644HCID 58677644, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

Compound 311 (48 mg, 0.01 mmol) was dissolved in TFA:H2O (3:1, 8 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography using EtOAc/petroleum ether (40-60)(v:v=1:1) as the eluent, affording the title compound as a yellow oil. 13C NMR (DMSO-d6) δ 193.5, 156.3, 150.1, 148.8, 137.5, 132.5, 132.3, 129.3, 126.6 (dd), 123.9 (dd), 122.9, 117.3, 116.1, 115.6, 112.1 (dd), 108.6, 105.1 (dd), 69.8, 62.5, 19.0

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6863bc157917488ba76f569cb03b8e02
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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