HCID 67275055, compound → HCID 10470395, compound

HRID 1696892Notes

Reaction equation

HRID 1696892 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:38])[C:19]([C:35]([OH:37])=[O:36])=[CH:20][N:21]3CC3C=CC(OC)=CC=3OC)=[C:16]([CH3:39])[C:15]=2[F:40])[CH2:10]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:38])[C:19]([C:35]([OH:37])=[O:36])=[CH:20][NH:21]3)=[C:16]([CH3:39])[C:15]=2[F:40])[CH2:10]1

Participants

3

Reactant 1

HCID 67275055HCID 67275055, compound

Product 1

HCID 10470395HCID 10470395, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 1F (334 mg) in trifluoroacetic acid (25 mL) was refluxed for 3 hours then cooled and concentrated. The concentrate was azeotroped with toluene and dissolved in water (250 mL); and this solution was washed with diethyl ether, filtered through a 0.45 μm syringe membrane filter, and lyophilized. NMR (300 MHz, DMSO-d6) δ 8.46 (s, 1H), 4.01-3.75 (m, 5H), 2.71 (m, 3H), 2.30 (m, 1H), 2.10 (m, 1H).

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. customThe concentrate was azeotroped with toluene
  4. dissolutiondissolved in water (250 mL)
  5. washand this solution was washed with diethyl ether
  6. filtrationfiltered through a 0.45 μm syringe membrane
  7. filtrationfilter

Sources & evidence

ORD record
ord-720d6d07048940b9b1ec3259a88a70dc
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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