HCID 22954557, compound → HCID 22954578, compound

HRID 1643375Notes

Reaction equation

HRID 1643375 reaction equation
[C:1]([NH:9][N:10]([CH2:36][CH2:37][C:38]([O:40]CC1C=CC=CC=1)=[O:39])[C:11]([N:13]1[C@H:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:16][CH2:15][N:14]1C(OCC1C=CC=CC=1)=O)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[C:1]([NH:9][N:10]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[C:11]([N:13]1[C@H:18]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:17][CH2:16][CH2:15][NH:14]1)=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22954557HCID 22954557, compound

Product 1

HCID 22954578HCID 22954578, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 260 (1.59 g, 2.47 mmol) in MeOH (142 ml) was treated with 10% Palladium on carbon (230.0 mg) and stirred under an atmosphere of H2 for 1.5 h. The mixture was filtered and the solvent evaporated to afford 1.04 g (100%) of a white foam. This was used in the next step without further purification: mp <40° C.; [α]D26 +1.6° (c 0.26, CH2Cl2); IR (KBr) 3422, 2977, 2986, 1728, 1677, 1486, 1445, 1396, 1369, 1309, 1228, 1155, 916, 716; 1H NMR (CDCl3) δ 10.0-9.7 (1H, brm), 7.86 (2H, d, J=7.5), 7.62-7.38 (3H, m), 7.3-5.6 (2H, brm), 4.57 (1H, brd, J=4.0), 4.05-3.77 (2H, m), 3.00-2.82 (1H, m), 2.80-2.43 (3H, m), 2.20-2.03 (1H, m), 2.00-1.47 (1H, m), 1.62-1.14 (11H, m); 13C NMR (CDCl3) δ 175.00, 171.17, 167.62, 160.68, 132.39, 131.77, 128.67, 127.38, 82.27, 54.38, 48.04, 46.35, 33.62, 28.02, 25.68, 21.61. MS (ES+) 443 (M+Na, 68%), 421 (M++1), 100), 365 (50), 131 (61).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-bcc9ef9f557343388c18d5b76e1c7830
Source dataset
uspto-grants-2012_02
Patent number
US08119631B2

Reaction notes

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