HCID 66686931, compound → HCID 66678676, compound

HRID 1471420Notes

Reaction equation

HRID 1471420 reaction equation
C([O:8][C@H:9]1[C@@:13]2([O:16][CH2:15][CH2:14]2)[C@H:12]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]2=[O:24])[O:11][C@@H:10]1[CH2:25][O:26]CC1C=CC=CC=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]1[C@@:13]2([O:16][CH2:15][CH2:14]2)[C@H:12]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]2=[O:24])[O:11][C@@H:10]1[CH2:25][OH:26]

Participants

4

Reactant 1

HCID 66686931HCID 66686931, compound

Product 1

HCID 66678676HCID 66678676, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent2×

Procedure

A mixture of 9 (50 mg, 0.111 mmol) in methanol (1 mL) and Pd(OH)2 (8 mg) was stirred under a hydrogen atmosphere at room temperature. After 4 hours, more Pd(OH)2 (30 mg) and methanol (1 mL) were added. The mixture was stirred vigorously under H2-atmosphere overnight. The catalyst was removed by filtration over decalite, and the solvent was removed by evaporation. The resulting residue was purified by silica gel chromatography eluted with 10% methanol in ethyl acetate to give the intermediate 10 as white powder (16.8 mg; 56%). HPLC Condition B, Rt: 1.98 min, m/z=271 (M+H)+. 1H NMR (400 MHz, D2O) δ ppm 7.65 (d, 1H, J=8.0 Hz), 6.11 (s, 1H), 5.82 (d, 1H, J=8.0 Hz), 4.46-4.61 (m, 2H), 4.06-4.13 (m, 1H), 3.87-3.95 (m, 1H), 3.69-3.77 (m, 2H), 2.62-2.73 (m, 1H), 2.48-2.58 (m, 1H).

Workup

  1. stirringThe mixture was stirred vigorously under H2-atmosphere overnight
  2. customThe catalyst was removed by filtration over decalite
  3. customthe solvent was removed by evaporation
  4. customThe resulting residue was purified by silica gel chromatography
  5. washeluted with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-ca68c8213cd54b28a877fcee349eee5b
Source dataset
uspto-grants-2015_04
Patent number
US09012428B2

Reaction notes

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