HCID 123288403, compound → HCID 123854094, compound

HRID 708908Notes

Reaction equation

HRID 708908 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([O:12][C:13]1[C:31]([F:32])=[CH:30][C:29]([N+:33]([O-])=O)=[CH:28][C:14]=1[CH2:15][N:16](C)[C:17](=O)OCC1C=CC=CC=1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][CH2:9][C@@H:10]([O:12][C:13]1[C:14]([CH2:15][NH:16][CH3:17])=[CH:28][C:29]([NH2:33])=[CH:30][C:31]=1[F:32])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 123288403HCID 123288403, compound

Product 1

HCID 123854094HCID 123854094, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of 33B (573 mg, 1.131 mmol) in MeOH (10 mL), was added 10% Pd—C (50 mg, 0.047 mmol). The mixture was evacuated and flushed with H2 (3×), then was stirred under an atmosphere of H2 for 8 h. The mixture was filtered and concentrated to give 33C (382 mg, 1.115 mmol, 99% yield) as a pale brown oil. MS (ESI) m/z: 343.1 [M+1]+. 1H NMR (400 MHz, chloroform-d) δ ppm 6.40 (1H, d, J=1.8 Hz) 6.33 (1H, dd, J=12.5, 2.8 Hz) 4.20 (1H, sxt, J=5.7 Hz) 3.62-3.79 (4H, m) 3.53 (2H, br. s.) 2.40 (3H, s) 1.25 (3H, d, J=6.3 Hz) 0.89 (9H, s) 0.05 (6H, s).

Workup

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

Sources & evidence

ORD record
ord-70a4b3be7f3741c1bb043ce71f320808
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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