HCID 86587575, compound → HCID 69973799, compound

HRID 481254Notes

Reaction equation

HRID 481254 reaction equation
[CH3:1][C@:2]12[C@H:54]3[CH2:55][C@H:52]([C:53]3([CH3:57])[CH3:56])[CH2:51][C@H:3]1[O:4][B:5]([C@@H:7]([NH:10][C:11]([C@H:13]1[N:17]3[C:18](=[O:40])[C:19]([N:22](CC4C=CC=CC=4)C(=O)OCC4C=CC=CC=4)=[CH:20][N:21]=[C:16]3[C@:15]([CH3:50])([CH2:41]/[CH:42]=[CH:43]/[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:14]1)=[O:12])[CH2:8][CH3:9])[O:6]2>CO.Cl.[Pd]>[CH3:1][C@:2]12[C@H:54]3[CH2:55][C@H:52]([C:53]3([CH3:56])[CH3:57])[CH2:51][C@H:3]1[O:4][B:5]([C@@H:7]([NH:10][C:11]([C@H:13]1[N:17]3[C:18](=[O:40])[C:19]([NH2:22])=[CH:20][N:21]=[C:16]3[C@:15]([CH3:50])([CH2:41][CH2:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:14]1)=[O:12])[CH2:8][CH3:9])[O:6]2

Participants

5

Reactant 1

HCID 86587575HCID 86587575, compound

Product 1

HCID 69973799HCID 69973799, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 116d in MeOH (2 mL), were added conc. HCl (3 drops) and 10% Pd-C (10 mg). The mixture was evacuated and flushed with H2 (3×), then stirred under an atmosphere of H2 for 45 min. The mixture was filtered and concentrated to afford 17.3 mg (96%) of 116e as the HCl salt. MS (ESI) 547.3 (M+H+), 569.3 (M+Na+), 545.2 (M−H+).

Workup

  1. customThe mixture was evacuated
  2. customflushed with H2 (3×)
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ce38086132c248eb966981b460cbf026
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

Loading…