HCID 85623257, compound → HCID 85623259, compound

HRID 1646932Notes

Reaction equation

HRID 1646932 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([O:13][C:14]1[C:15]([C:20]2[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH:21]=2)=[N:16][CH:17]=[CH:18][N:19]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(O)C.O=[Pt]=O>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([O:13][C:14]1[C:15]([CH:20]2[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[N:16][CH:17]=[CH:18][N:19]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 85623257HCID 85623257, compound

Product 1

HCID 85623259HCID 85623259, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.29 g of the free base of (14) (0.001 mol) and 0.15 g PtO2 in 50 ml of ethanol was hydrogenated overnight at 60 psi of H2. The catalyst was filtered off and the solvent evaporated to give 0.22 g of a clear liquid. The oxalate salt (15), 0.15 g, crystallized from ethyl acetate as a floculant colorless solid, mp 137°-138° C. NMR ppm (CDCl3) 0.9 (3H, t), 1.3-1.55 (6H, m), 1.6-1.9 (4H, m), 2.1 (2H, m), 2.45 (1H, m), 3.25 (1H, m), 3.35-3.65 (4H, m), 3.72 (1H, t), 4.25 (1H, q), 4.35 (2H, t), 8.05 (1H, d), 8.1 (1H, d). Anal. C17H27N3O-C2H2O4 requires C: 60.14; H: 7.70; N: 11.07%. Found C: 60.29; H: 7.91; N: 10.85%.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-211cf6237fd54808b8b41d40c4dac1c0
Source dataset
uspto-grants-1993_01
Patent number
US05182283

Reaction notes

Loading…