Trifluoroacetic acid → HCID 58997409, compound

HRID 1592010Notes

Reaction equation

HRID 1592010 reaction equation
C([O:5][C:6]([C:8]1[CH:32]=[CH:31][C:11]([CH2:12][O:13][C:14](=[O:30])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:26][C:25](=[O:27])[NH:24][S:23]3(=[O:29])=[O:28])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14](=[O:30])[C:15]2[CH:16]=[CH:17][C:18]([CH2:21][N:22]3[CH2:26][C:25](=[O:27])[NH:24][S:23]3(=[O:28])=[O:29])=[CH:19][CH:20]=2)=[CH:31][CH:32]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67140081HCID 67140081, compound

Product 1

HCID 58997409HCID 58997409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title C compound, 4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 4-t-butoxycarbonyl-benzyl ester (119 mg, 0.19 mmol) is dissolved in CH2Cl2 (5 mL) and then added TFA (5 mL, 64.9 mmol). This is stirred for 2 h and then concentrated under reduced pressure. The residue is suspended in MeCN:water (6:4) (12 mL), centrifuged, decanted and filtered through a 0.1 micron Acrodisc filter. The resulting mixture is loaded onto a preparative reverse phase HPLC column (YMC CombiPrep Pro C18, 50×20 mm I.D., particle size S-5 micron, 12 nM) in 6 aliquots and eluted at 30 mL/min with a gradient of 90:10 (water containing 0.1% TFA: MeCN) at 0 min to 10:90 at 5 min. Then held at 10:90 until 7 min. Fractions containing product are combined and concentrated by lyophilization to yield 4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 4-carboxy-benzyl ester as a white amorphous solid: [M−1]−=403.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customcentrifuged, decanted
  3. filtrationfiltered through a 0.1 micron Acrodisc
  4. filtrationfilter
  5. washeluted at 30 mL/min with a gradient of 90:10 (water containing 0.1% TFA: MeCN) at 0 min to 10:90 at 5 min
  6. waitThen held at 10:90 until 7 min
  7. additionFractions containing product
  8. concentrationconcentrated by lyophilization

Sources & evidence

ORD record
ord-7be1f1cc7cac4d3ca987eb298eef2b96
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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