Trifluoroacetic acid → HCID 178500641, compound

HRID 1934814Notes

Reaction equation

HRID 1934814 reaction equation
[CH3:1][O:2][C:3](=[O:58])[CH:4]([NH:9][C:10](=[O:57])[CH2:11][N:12]1[C:16]([CH3:27])([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:15](=[O:28])[N:14]([CH2:29][CH2:30][CH2:31][C:32]2[N:33]=[CH:34][N:35](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:36]=2)[C:13]1=[O:56])[CH2:5][CH2:6][S:7][CH3:8].C([SiH](C(C)C)C(C)C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:58])[CH:4]([NH:9][C:10](=[O:57])[CH2:11][N:12]1[C:16]([CH3:27])([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:15](=[O:28])[N:14]([CH2:29][CH2:30][CH2:31][C:32]2[N:33]=[CH:34][NH:35][CH:36]=2)[C:13]1=[O:56])[CH2:5][CH2:6][S:7][CH3:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 53880154HCID 53880154, compound

Product 1

HCID 178500641HCID 178500641, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.11 g(0.13 mmol) of 2-(2-{3-[3-(1-triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-2,4-dioxo-imidazolidin-1-yl}-acetylamino)-4-methylsulfanyl-butyric acid methyl ester prepared in Example 1-3) and 0.053 ml(0.26 mmol) of triisopropylsilane were dissolved in 5 ml of methylene chloride. Then, 5 ml of trifluoroacetic acid was added thereto and the resulting solution was stirred for one hour at room temperature. The organic solvent was removed under reduced pressure and saturated potassium carbonate[K2CO3] solution was added. The solution was extracted with 10 of ethyl acetate and the solvent was removed under reduced pressure. The residue was subjected to chromatography using a solvent mixture of methanol-methylene chloride(5:95) as the eluent to obtain 0.068 g(Yield: 95%) of the title compound.

Workup

  1. customThe organic solvent was removed under reduced pressure and saturated potassium carbonate[K2CO3] solution
  2. additionwas added
  3. extractionThe solution was extracted with 10 of ethyl acetate
  4. customthe solvent was removed under reduced pressure
  5. additiona solvent mixture of methanol-methylene chloride(5:95) as the eluent

Sources & evidence

ORD record
ord-3f00bf14b8f941118dfbdb5567d8e90d
Source dataset
uspto-grants-2002_05
Patent number
US06384061B1

Reaction notes

Loading…