HCID 67271708, compound → HCID 67271814, compound

HRID 601724Notes

Reaction equation

HRID 601724 reaction equation
[CH2:1]([C@H:5]1[CH2:9][CH2:8][N:7]([C@@H:10]([CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:11]([O:13][C@@H:14]([CH2:36][C:37]2[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[CH:38]=2)[C@@H:15]([C@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][N:18]2CC2C=CC(OC)=CC=2)[OH:16])=[O:12])[C:6]1=[O:53])[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([C@H:5]1[CH2:9][CH2:8][N:7]([C@@H:10]([CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:11]([O:13][C@@H:14]([CH2:36][C:37]2[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[CH:38]=2)[C@H:15]([OH:16])[C@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][NH:18]2)=[O:12])[C:6]1=[O:53])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 67271708HCID 67271708, compound

Product 1

HCID 67271814HCID 67271814, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the compound of Step (A) in MeOH was added 10% Pd/C. The mixture was shaken under H2 in a Parr shaker, and after 3 pump/flush cycles, the reaction was allowed to shake overnight. The reaction was filtered through a 0.45 μm filter, and solvents removed in vacuo. The residue was injected onto a reverse-phase HPLC column (XTERRA S5 19×100 mm, gradient from 10% MeOH/H2O to 90% MeOH/H2O, containing 0.1% TFA) to afford, after solvent removal, pure product. 1H NMR (500 MHz, CD3OD) δ ppm 0.93 (t, J=7.02 Hz, 3H) 1.08-1.22 (m, 1H) 1.24-1.46 (m, 5H) 1.64-1.78 (m, 1H) 1.78-1.99 (m, 2H) 1.99-2.12 (m, 1H) 2.20-2.44 (m, 3H) 2.77 (dd, J=14.04, 11.29 Hz, 1H) 2.98-3.09 (m, 1H) 3.11-3.23 (m, 2H) 3.23-3.43 (m, 2H) 3.51-3.60 (m, 1H) 4.03 (dd, J=9.77, 2.14 Hz, 1H) 4.17-4.48 (m, 4H) 6.73-6.82 (m, 1H) 6.82-6.92 (m, 4H) 7.06-7.32 (m, 7H). HPLC retention time: 1.84 min (method C). MS (ESI) (M+H)+ 604.

Workup

  1. customafter 3 pump/flush cycles
  2. filtrationThe reaction was filtered through a 0.45 μm
  3. filtrationfilter
  4. customsolvents removed in vacuo
  5. additionThe residue was injected onto a reverse-phase HPLC column (XTERRA S5 19×100 mm, gradient from 10% MeOH/H2O to 90% MeOH/H2O, containing 0.1% TFA)
  6. customto afford
  7. customafter solvent removal, pure product

Sources & evidence

ORD record
ord-1742ad2819c34fa8a3832ecd4fc4fc51
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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