Trifluoroacetic acid → HCID 66658525, compound

HRID 420833Notes

Reaction equation

HRID 420833 reaction equation
CCN([CH2:6][CH2:7][NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)=[O:10])CC.[CH:18]1C=C[C:21]([CH2:24][O:25][C@H:26]([C:32]([OH:34])=[O:33])[C@H:27]([NH2:31])[C:28]([OH:30])=[O:29])=[CH:20][CH:19]=1.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[I:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]([NH:8][C:7]2[CH:6]=[C:21]([CH:20]=[CH:19][CH:18]=2)[CH2:24][O:25][C@H:26]([C:32]([OH:34])=[O:33])[C@@H:27]([C:28]([OH:30])=[O:29])[NH2:31])=[O:10])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131729395HCID 131729395, compound

Product 1

HCID 66658525HCID 66658525, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Protected I-BzA-TBOA (120 mg, 0.17 mmol) was dissolved in 1 ml of chloroform. After adding 1 ml of TFA, the obtained mixture was stirred for 24 hours. Then the solvent was distilled off and water was added to the residue followed by repeated freeze-drying. Thus, 78 mg (76%) of the title compound was obtained. Amorphous product; [α]D −37.7° (c 0.34, CHCl3); 1H NMR (CDCl3, 400 MHz); ™4.30 (d, 1 H, J=5.0 Hz), 4.45 (d, 1 H, J=11.0 Hz), 4.68 (d, 1 H, J=11.0 Hz), 7.14 (d, 1 H, J=7.5 Hz), 7.30 (t, 1 H, J=8.0 Hz), 7.59 (s, 1 H), 7.64 (d, 1 H, J=8.5 Hz), 7.67 (d, 2 H, J=7.5 Hz), 7.86 (d, 2 H, J=7.5 Hz).

Workup

  1. distillationThen the solvent was distilled off
  2. additionwater was added to the residue
  3. customby repeated freeze-drying

Sources & evidence

ORD record
ord-165f1e2c0bbf438ca3a67d5d4ac5155d
Source dataset
uspto-grants-2012_01
Patent number
US08097654B2

Reaction notes

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