Trifluoroacetic acid → HCID 178461493, compound

HRID 1604249Notes

Reaction equation

HRID 1604249 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:20]/[O:21][CH:22]([CH2:32][NH:33]C(OC(C)(C)C)=O)[CH2:23][NH:24]C(OC(C)(C)C)=O)/[C:7]([NH:9][C@H:10]1[C@H:13]([CH3:14])[N:12]([S:15]([OH:18])(=[O:17])=[O:16])[C:11]1=[O:19])=[O:8].[K].[F:42][C:43]([F:48])([F:47])C(O)=O>C(Cl)Cl>[OH:18][S:15]([C:43]([F:48])([F:47])[F:42])(=[O:16])=[O:17].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:20]/[O:21][CH:22]([CH2:32][NH2:33])[CH2:23][NH2:24])/[C:7]([NH:9][C@H:10]1[C@H:13]([CH3:14])[N:12]([S:15]([OH:18])(=[O:17])=[O:16])[C:11]1=[O:19])=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5462222PotassiumHCID 15458137HCID 15458137, compound

Product 1

HCID 178461493HCID 178461493, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3S)-trans-3-[(E)-2-(2-thienyl)-2-{1,3-di(t-butoxycarbonylamino)-prop-2-oxyimino} acetamido]-4-methyl-2-oxoazetidine-1-sulfonic acid, potassium salt (step 4, Example 2, 4.04 gm, 5.2756 mmol) in methylene chloride (12 ml) cooled to -5° C. was added trifluoroacetic acid (18 gm, 156.890 mmol) dropwise and stirred at this temperature for 4 hr. The mixture was diluted with methylene chloride and concentrated under reduced pressure to give a foam which was triturated with ether to afford a white solid. Purification of the product over HP-20 column with acetonitrile-water (1:9) as eluant and freeze-drying of the desired fractions gave the target compound as a white solid, 2.15 gm (66% yield). 1H-NMR (DMSO-d6): δ 9.04 (d, 1H, J=8.05 Hz); 7.96-8.05 (m, 8H); 7.24 (t, 1H, J=4.5 Hz); 4.70-4.90 (m, 1H); 4.53 (dd, 1H, J=2.68 and 8.04 Hz); 3.70-3.84 (m, 1H); 3.18-3.40 (m, 4H); 1.44 (d, 3H, J=6.07 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a foam which
  3. customwas triturated with ether
  4. customto afford a white solid
  5. customPurification of the product over HP-20 column with acetonitrile-water (1:9) as eluant
  6. customfreeze-drying of the desired fractions

Sources & evidence

ORD record
ord-8b9d0b903642402e98fa996e3767b86b
Source dataset
uspto-grants-1999_11
Patent number
US05994340

Reaction notes

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