HCID 10471772, compound → HCID 12082818, compound

HRID 508604Notes

Reaction equation

HRID 508604 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:4]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:2]([C:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 10471772HCID 10471772, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 12082818HCID 12082818, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 8b (3 g, 9.1 mmol) and 3 g of powdered 4 Å molecular sieves in 150 mL of DCM, was added PCC (2.94 g, 13.7 mmol) at room temperature. After 6 hours, the reaction mixture was filtered through a 0.75-in. pad of Celite. The filtrate was concentrated in vacuo then the residue was purified by column chromatography to afford the titled compound (2.1 g, 70%) as a white solid. mp 177.3-179.8° C. 1H NMR (300 MHz, DMSO-d6): δ 10.03 (s, 1H), 7.88 (d, J=8 Hz, 2H), 7.61-7.49 (m, 4H), 7.48-7.37 (m, 3H), 7.35-7.26 (m, 2H), 7.20 (s, 1H).

Workup

  1. filtrationthe reaction mixture was filtered through a 0.75-in
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1bc4d0f4a23a422d92c3eed2ce59dbc1
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

Loading…