HCID 10874277, compound → HCID 11025186, compound

HRID 1359173Notes

Reaction equation

HRID 1359173 reaction equation
[CH3:1][O:2][C:3]([C@:5]12[CH2:16][C@@:15]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:17]([O:19]CC3C=CC=CC=3)=[O:18])[C:14](=[O:34])[N:6]1[C@H:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[O:8][CH2:9]2)=[O:4]>C(O)(C)(C)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C@:5]12[CH2:16][C@@:15]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:17]([OH:19])=[O:18])[C:14](=[O:34])[N:6]1[C@H:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[O:8][CH2:9]2)=[O:4]

Participants

4

Reactant 1

HCID 10874277HCID 10874277, compound

Product 1

HCID 11025186HCID 11025186, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

Compound 11 (250 mg, 0.54 mmol) was dissolved in t-butanol (10 mL), then 20% Pd(OH)2/C (90 mg) was added, and the mixture was hydrogenated at 1 bar and room temperature overnight. The catalyst was filtered off, and the solvent was removed under vacuum to give the product 13 (200 mg, 100%): mp >133° C. (decomp.; from hexane/EtOAc); [α]D+9.1° (c 0.4 CHCl3); IR (KBr) 3141, 2973, 1736, 1718 cm−1; 1H NMR δ7.33-7.14 (m, 5H), 6.5 (br, 1H), 4.84 (s, 1H), 4.80 (d, 1H, J=8.7 Hz), 3.77 (s, 3H), 3.54-3.38 (m, 3H), 2.67 (d, 1H, J=14.7 Hz ), 2.43 (d, 1H, J=14.7 Hz), 0.93 (s, 9H); 13C NMR δ179.77, 172.03, 171.80, 134.52, 130.02, 128.50, 127.70, 97.94, 74.25, 69.22, 60.24, 53.09, 42.94, 35.34, 35.15, 24.93; MS m/z (%) 331 (0.3), 274 (36), 58 (72), 43 (100). Anal. (C20H25NO6) Calcd: C, 63.99; H, 6.71; N, 3.73. Found; C, 64.33; H, 6.47; N, 3.57.

Workup

  1. customwas hydrogenated at 1 bar and room temperature overnight
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6f31661a6e624633a9ec668d795efac5
Source dataset
uspto-grants-2003_07
Patent number
US06599940B2

Reaction notes

Loading…