HCID 58677558, compound → HCID 58677543, compound

HRID 1012661Notes

Reaction equation

HRID 1012661 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[CH3:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH:27]2[CH2:31][O:30]C(C)(C)[O:28]2)[CH:22]=[CH:21][C:20]=1[F:34])=[O:18]>C(O)(C(F)(F)F)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[CH3:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH:27]([OH:28])[CH2:31][OH:30])[CH:22]=[CH:21][C:20]=1[F:34])=[O:18]

Participants

3

Reactant 1

HCID 58677558HCID 58677558, compound

Product 1

HCID 58677543HCID 58677543, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

Compound 320 (31 mg, 0.07 mmol) was dissolved in TFA:H2O (3:1, 10 mL) and stirred at RT for 1 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography using DCM/MeOH (v:v=99.5:0.5 to 98.5:1.5) as the eluent, affording the title compound as oil. 13C NMR (CDCl3) δ 190.5, 155.4 (d), 154.6 (d), 148.9, 136.7, 134.9, 134.3, 133.3, 131.2, 130.4, 128.5, 128.2 (d), 127.1, 125.1, 120.2 (d), 117.1 (d), 115.7, 115.2 (d), 112.5, 70.3, 69.9, 63.5, 17.9

Workup

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

Sources & evidence

ORD record
ord-8812c0ebc5c6400494b50c295785cced
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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