Ethyl Acetate → HCID 131720196, compound

HRID 1378446Notes

Reaction equation

HRID 1378446 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH:27]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][C:38]#C)[CH:31]=4)[CH2:26][CH2:25]3)=[O:19])[CH:12]=2)[C:9]([C:40]([O:42][CH3:43])=[O:41])=[C:8]([CH3:44])[NH:7][C:6]=1[CH3:45])=[O:4].[CH3:46]COC(C)=O>[Pd]>[CH3:45][C:6]1[NH:7][C:8]([CH3:44])=[C:9]([C:40]([O:42][CH3:43])=[O:41])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH:27]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH:37]([CH3:38])[CH3:46])[CH:31]=4)[CH2:26][CH2:25]3)=[O:19])[CH:12]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 88383137HCID 88383137, compound

Product 1

HCID 131720196HCID 131720196, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of the product of Example 51 (316 mg, 0.519 mmol) and 81 mg of 10% Pd/C in EtOAc (65 mL) was shaken under 50 psi of H2 on a Parr Hydrogenator for 3 h. The suspension was then filtered through Celite and the filtrate concentrated in vacuo to give 325 mg of the product as a clear oil. This residue was purified by preparative HPLC (Zorbax-RX-C8 column; 45% MeCN/55% 0.1% TFA H2O; 4.2 mL/min) and the free base subsequently converted to the HCl salt to furnish the product as a colorless foam: mp 110°-130° C. (sintered); 1H NMR (CDCl3) δ10.62 (br s, 1H). 8.53 (br s, 1H), 7.34 (d, 1H, J=7.6 Hz), 7.12 (m, 3H), 7.00 (t, 1H, J=7.6 Hz), 6.86 (d, 1H, J=7.5 Hz), 6.68 (m, 4H), 4.90 (s, 1H), 3.82 (t, 2H, J=6.5 Hz), 3.54 (s, 6H), 3.45 (m, 2H), 3.20 (m, 2H), 2.75 (m, 4H), 2.62 (m, 3H), 2.25 (s, 6H), 1.92 (m, 4H), 1.72 (h, 2H, J=6.8 Hz), and 0.95 (t, 3H, J=7.3 Hz); 13C NMR (CDCl3) δ168.4, 159.4, 157.1, 148.8, 145.5, 144.4, 139.6, 129.8, 128.5, 122.0, 118.7, 118.1, 117.2, 113.6, 112.5, 102.9, 69.5, 55.2, 53.3, 51.0, 40.2, 39.1, 36.7, 30.2, 25.1, 22.6, 19.2, and 10.5. Anal. Calcd for C35H46N4O6.HCl.0.45H2O: C, 63.37; H, 7.28; N, 8.45. Found: C, 63.37; H, 7.40; N, 8.28.

Workup

  1. filtrationThe suspension was then filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-a8fb1db7cbd043a6b7cc049ecc166317
Source dataset
uspto-grants-1997_09
Patent number
US05668151

Reaction notes

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