Trifluoroacetic acid methylene chloride → HCID 66726889, compound

HRID 710465Notes

Reaction equation

HRID 710465 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:5]2.[C:30]([C:34]([OH:36])=[O:35])([F:33])([F:32])[F:31].C(Cl)Cl>CCO>[F:31][C:30]([F:33])([F:32])[C:34]([OH:36])=[O:35].[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][NH:6][CH2:5]2

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 667262485-Iodo-2-tritylisoindoline

Product 1

HCID 66726889HCID 66726889, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A product of Example 2, Step C (1.32 g; 2.71 mmol) in 60% CF3CO2H/CH2Cl2 (10 ml) was stirred for 10 min at room temperature under N2, then diluted to 30 ml with EtOH and stirred for additional 15 min. This was evaporated to dryness under reduced pressure and the residue was dissolved in EtOAc (10 ml) and hexane (20 ml) was added. After standing overnight at room temperature, the precipitate formed was filtered off, washed with hexane and dried to give the title compound (0.77 g; 79%), as off white solid, which was used in the next step without further purification. 1H-NMR (CDCl3) 4.47 (5, 2H); 4.51 (s, 2H); 6.7-6.8 (m, 1H); 7.0-7.21 (m, 1H); 7.4-7.7 (m, 1H); 10.6 (broad s, 1H).

Workup

  1. customThis was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (10 ml)
  3. additionhexane (20 ml) was added
  4. waitAfter standing overnight at room temperature
  5. customthe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-541ee45f5389412f9d37e8b550b41446
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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