HCID 69981834, compound → HCID 69949710, compound

HRID 1935627Notes

Reaction equation

HRID 1935627 reaction equation
C(OC([N:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])=O)C1C=CC=CC=1>[Pd].C(O)C>[Si:33]([O:32][CH2:31][CH:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[C:16]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])[CH:15]=2)[NH:11]1)([C:36]([CH3:39])([CH3:37])[CH3:38])([CH3:34])[CH3:35]

Participants

4

Reactant 1

HCID 69981834HCID 69981834, compound

Product 1

HCID 69949710HCID 69949710, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product from Step 8 (2.2 g, 0.0040 mol), 10% palladium-on-carbon catalyst (0.4 g) and ethanol (150 ml) is hydrogenated at an initial pressure of 44 p.s.i. for 2 h. The catalyst is removed by filtration through celite and the filtrate is concentrated. The residue is dissolved in CH2Cl2, filtered and concentrated to give the titled product: MS (ES) m/z 420 (M+H+), 442 (M+Na+); 1H NMR (300 MHz, CDCl3) δ0.05 (s, 6H), 0.89 (s, 9H), 2.02 (s, 3H), 2.63 (q, 1H), 3.09 (q, 1H), 3.53 (m, 3H), 3.71 (m, 2H), 4.23 (broad s, 1H), 4.71 (m, 1H), 6.14 (t, 1H), 6.58 (d, 1H), 6.98 (d, d, 1H), 7.26 (d, 1H).

Workup

  1. customThe catalyst is removed by filtration through celite
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in CH2Cl2
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-622ee5b538d34b7cbbe5a718015f39da
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

Loading…