Trifluoroacetic acid → HCID 86659505, compound

HRID 885708Notes

Reaction equation

HRID 885708 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][N:25]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:22])[NH:20][OH:21])=[CH:15][CH:14]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][N:25]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([NH:20][OH:21])=[O:22])=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 123919966HCID 123919966, compound

Product 1

HCID 86659505HCID 86659505, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl1-(4-(hydroxycarbamoyl)benzylamino)-3-(5-hydroxypyridin-2-yl)-1-oxopropan-2-ylcarbamate (0.10 g, 0.19 mmol) with 1 mL of TFA in 10 mL of CH2Cl2 (25 mL) was stirred for 4 h at room temperature. The solvent was evaporated (monitored by TLC). The residue was purified by chromatography to give oily Compound 10 (0.045 g, 71%). NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 3.08 (m, 2H, CH2), 4.20 (m, 2H, CH2), 4.36 (m, 1H, CH), 7.08-7.28 (m, 4H, Ar—H), 7.62-7.70 (m, 2H, Ar—H), 7.82-7.88 (m, 1H, Ar—H), 8.96 (m, 2H, NH2), 9.13 (br, 1H, NH), 9.97 (br, 1H, NH), 11.15 (br, 1H, OH).

Workup

  1. customThe solvent was evaporated (monitored by TLC)
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-cb14baa2781d4d84bfc4b4f5a4732741
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

Loading…