HCID 54482325, compound → HCID 19039922, compound

HRID 1684612Notes

Reaction equation

HRID 1684612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C:7](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)[C:6]2=[O:23]>CO.O1CCCC1.[Pd]>[NH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][CH:7]1[C:6](=[O:23])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[O:9][CH2:8]1

Participants

5

Reactant 1

HCID 54482325HCID 54482325, compound

Product 1

HCID 19039922HCID 19039922, compoundYield 107%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.20 g (32.8 mmol) of the product of Example 1 and 2 g of 10% Pd/C in 200 mL CH3OH and 200 mL tetrahydrofuran was shaken on a Parr (trademark) hydrogenation apparatus at 25 psi H2 at room temperature. After 30 minutes the reaction mixture was filtered through diatomaceous earth (Celite [trademark]), and the filtrate concentrated in vacuo to yield 9.94 g of a yellow solid. Silica gel chromatography eluting with 5% ethyl acetate-CH2Cl2 afforded 8.53 g of a yellow solid (92%). A small sample was recrystallized from ethyl acetate-hexane to obtain analytical data. M.p. 137°-139° C.; MS: 283M+, 107 Base; 1H NMR (AC 300, CDCl3): δ4.3 (1H, m); 4.15 (1H, m), 3.82 (3H, s); 3.7 (1H, m); 3.67 (1H, m); 2.9 (1H, m); 2.6 (1H, m); IR: 3430, 3250, 1660 cm-1. Analysis: calculated: C. 72.07, H 6.05, N 4.94%; found: C: 71.69, H 6.01, N 4.96%.

Workup

  1. filtrationAfter 30 minutes the reaction mixture was filtered through diatomaceous earth (Celite [trademark])
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-635112a2468d49d284d3b22c31367e2c
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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