HCID 86701135, compound → HCID 86701134, compound

HRID 1403083Notes

Reaction equation

HRID 1403083 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[C:15]([C:20]4[CH:21]=[C:22]([CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[CH:23]=[N:24][CH:25]=4)[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[NH:36][CH:37]1[CH2:42][CH2:41][CH:40]([OH:43])[CH2:39][CH2:38]1)(=[O:3])[NH2:2]>C(O)(C(F)(F)F)=O>[NH2:28][CH2:27][CH2:26][C:22]1[CH:21]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[CH:13]=[CH:12][N:11]=[C:10]3[C:7]2[CH:8]=[CH:9][C:4]([C:1]([NH2:2])=[O:3])=[C:5]([NH:36][CH:37]3[CH2:38][CH2:39][CH:40]([OH:43])[CH2:41][CH2:42]3)[CH:6]=2)[CH:25]=[N:24][CH:23]=1

Participants

3

Reactant 1

HCID 86701135HCID 86701135, compound

Product 1

HCID 86701134HCID 86701134, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound (19) (0.047 g) in TFA was stirred at room temperature for 3 hours. The solvent was distilled off, and chloroform was added to the residue. The reaction solution was neutralized with an aqueous sodium bicarbonate solution and partitioned into organic and aqueous layers. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, and diethyl ether was added to the residue. The deposit was filtrated to obtain compound (20) (0.022 g, yield: 60%) as a white solid.

Workup

  1. distillationThe solvent was distilled off
  2. additionchloroform was added to the residue
  3. custompartitioned into organic and aqueous layers
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. additiondiethyl ether was added to the residue
  8. filtrationThe deposit was filtrated

Sources & evidence

ORD record
ord-027bf963413a4bd39555a5a7a87137c1
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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