Trifluoroacetic acid → 5-[[5-[(E)-N-hydroxy-C-(3-methylbutyl)carbonimidoyl]thiophen-2-yl]methyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 1592006Notes

Reaction equation

HRID 1592006 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][C:13]2[S:14][C:15]([C:18](=[N:24][OH:25])[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[S:7]1(=[O:27])=[O:26].C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:25]/[N:24]=[C:18](/[C:15]1[S:14][C:13]([CH2:12][N:8]2[S:7](=[O:27])(=[O:26])[NH:6][C:10](=[O:11])[CH2:9]2)=[CH:17][CH:16]=1)\[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865910402-(2,4-Dimethoxy-benzyl)-5-(5-{1-[hydroxyimino]-4-methylpentyl}-thiophen-2-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 589973975-[[5-[(E)-N-hydroxy-C-(3-methylbutyl)carbonimidoyl]thiophen-2-yl]methyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title E compound, 2-(2,4-dimethoxy-benzyl)-5-(5-{1-[-hydroxyimino]-4-methyl-pentyl}-thiophen-2-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (40 mg, 0.08 mmol) is stirred in equal volumes of CH2Cl2 and TFA (4 mL) at RT for 3 h. The volatiles are evaporated and the residue is stirred in equal volumes of MeCN/water (5 mL) for 15 min. The mixture is filtered through a 0.2, Acrodisc and the solvents are evaporated to dryness. The residue is triturated from hexane/Et2O (4:1) to afford 5-(5-{1-[(E)-hydroxyimino]-4-methyl-pentyl}-thiophen-2-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a light pink solid: [M+1]+=346.

Workup

  1. customThe volatiles are evaporated
  2. filtrationThe mixture is filtered through a 0.2, Acrodisc
  3. customthe solvents are evaporated to dryness
  4. customThe residue is triturated from hexane/Et2O (4:1)

Sources & evidence

ORD record
ord-fd060ad58079489f92069f131cddfbe0
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

Loading…