Trifluoroacetic acid → HCID 59327346, compound

HRID 1927572Notes

Reaction equation

HRID 1927572 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[C:29]([Cl:30])=[CH:28][CH:27]=[C:26]([NH:31][C:32]3[C:35](=[O:36])[C:34](=[O:37])[C:33]=3[NH:38][C@@H:39]([C@H:42]3[CH2:46][CH2:45][C@@H:44]([CH3:47])[O:43]3)[CH2:40][CH3:41])[C:25]=2[OH:48])(=[O:23])=[O:22])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:30][C:29]1[CH:28]=[CH:27][C:26]([NH:31][C:32]2[C:35](=[O:36])[C:34](=[O:37])[C:33]=2[NH:38][C@@H:39]([C@H:42]2[CH2:46][CH2:45][C@@H:44]([CH3:47])[O:43]2)[CH2:40][CH3:41])=[C:25]([OH:48])[C:24]=1[S:21]([N:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1)(=[O:22])=[O:23]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59327351HCID 59327351, compound

Product 1

HCID 59327346HCID 59327346, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

0.4 ml of TFA are added dropwise to an ice-cooled solution of 54 mg of 4-(6-chloro-2-hydroxy-3-{2-[(R)-1-((2R,5R)-5-methyl-tetrahydrofuran-2-yl)-propylamino]-3,4-dioxo-cyclobut-1-enylamino}-benzene sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (Ex. 17) in 1 ml of dry DCM under an inert atmosphere of nitrogen. After stirring at rt for 4 hours, a reaction mixture obtained is diluted with 25 ml DCM and 25 ml NaHCO3(aq) are added. An organic portion is separated and washed with 3×NaHCO3(aq), dried over MgSO4 and solvent is evaporated. The title compound is obtained. MH+ 513.

Workup

  1. customa reaction mixture obtained
  2. additionare added
  3. customAn organic portion is separated
  4. washwashed with 3×NaHCO3(aq)
  5. dry with materialdried over MgSO4 and solvent
  6. customis evaporated

Sources & evidence

ORD record
ord-a2d279a9896f4eac97e7bb1143c0a872
Source dataset
uspto-grants-2012_05
Patent number
US08183281B2

Reaction notes

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