HCID 67962991, compound → HCID 67962996, compound

HRID 1426274Notes

Reaction equation

HRID 1426274 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C@@H:14]([C:23](OCC(F)(F)F)=[O:24])[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([N+:31]([O-:33])=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C=CC=CC=1.[Pt]>[C:19]([O:18][C:16](=[O:17])[NH:15][C@@H:14]1[C:23](=[O:24])[N:31]([OH:33])[C:10]2=[N:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:12]=[C:11]2[CH2:13]1)([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 67962991HCID 67962991, compound

Product 1

HCID 67962996HCID 67962996, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1049PyridineSolvent

Procedure

To a solution of C8 (110 mg, 0.233 mmol) in pyridine (10 mL) was added 5% platinum on carbon (35 mg, 0.0090 mmol), and the reaction was subjected to hydrogenation at 30 psi for 3 hours on a Parr shaker. After filtration through Celite, the filter pad was rinsed with EtOAc (10 mL) and the combined filtrates were concentrated in vacuo. Purification using silica gel chromatography (Gradient: 0% to 100% EtOAc in heptane) provided C9 as a solid. Yield: 55 mg, 0.15 mmol, 64%. LCMS m/z 359.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9H), 2.49 (br dd, J=14, 14 Hz, 1H), 3.30 (br dd, J=14, 7 Hz, 1H), 4.20-4.29 (m, 1H), 5.21 (AB quartet, JAB=15.2 Hz, ΔνAB=11.1 Hz, 2H), 5.61 (br s, 1H), 7.07-7.08 (m, 1H), 7.14-7.20 (m, 2H), 7.29-7.36 (m, 3H), 10.74 (br s, 1H).

Workup

  1. filtrationAfter filtration through Celite
  2. washthe filter pad was rinsed with EtOAc (10 mL)
  3. concentrationthe combined filtrates were concentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-8000b91b18aa4b7390de78d6c8562dec
Source dataset
uspto-grants-2015_01
Patent number
US08933095B2

Reaction notes

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