Trifluoroacetic acid → HCID 15463352, compound

HRID 1636879Notes

Reaction equation

HRID 1636879 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([NH:5][C:6]1[S:7][C:8]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[C:9]([CH3:18])[C:10]=1[C:11]([O:13]C(C)(C)C)=[O:12])=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:22]([O:21][C:19]([C:8]1[S:7][C:6]([NH:5][C:3]([C:2]([F:1])([F:29])[F:30])=[O:4])=[C:10]([C:11]([OH:13])=[O:12])[C:9]=1[CH3:18])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15463351HCID 15463351, compound

Product 1

HCID 15463352HCID 15463352, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound prepared in Example 5 (155 mg, 0.34 mmol) was dissolved in DCM (2.5 ml) and TFA (3 ml) was added dropwise. After 18 h, the reaction was concentrated. The crude solid was partitioned between CHCl3 and H2O. The layers were separated and the aqueous layer was extracted with CHCl3 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated to yield 130 mg of a white solid (99%). 1H-NMR (CDCl3) 2.83 (s, 3H), 5.34 (s, 2H), 7.40 (m, 5H); 13C-NMR (CDCl3)); mp-179-183° C.

Workup

  1. concentrationthe reaction was concentrated
  2. customThe crude solid was partitioned between CHCl3 and H2O
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CHCl3 (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a3b2b92eb6445859cc82d8776698124
Source dataset
uspto-grants-2000_03
Patent number
US06037340

Reaction notes

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