HCID 117974686, compound → HCID 117974974, compound

HRID 1776103Notes

Reaction equation

HRID 1776103 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([C@H:11]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C@@H:15]([O:29][CH2:30][CH:31]=[CH2:32])[C@H:14]([CH3:33])[O:13][C:12]1=[O:34])[CH2:8][O:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:35])[N:7]([C@H:11]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C@@H:15]([O:29][CH2:30][CH2:31][CH3:32])[C@H:14]([CH3:33])[O:13][C:12]1=[O:34])[CH2:8][O:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 117974686HCID 117974686, compound

Product 1

HCID 117974974HCID 117974974, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A vial was charged with 5 wt % Pd/C (26.0 mg, 0.012 mmol) and a solution of tert-butyl((3S,7R,8R,9S)-8-(allyloxy)-7-(4-methoxybenzyl)-9-methyl-2-oxooxonan-3-yl)(methoxymethyl)carbamate (200 mg, 0.407 mmol) in EtOAc (1 mL). The vial was evacuated and backfilled with H2 (3×) and then stirred vigorously under one atmosphere of H2 (balloon) at room temperature for 15 h. The reaction mixture was filtered through a plug of Celite® and concentrated to the title compound as a colorless oil (168 mg, 84%) IR (neat) 3368, 2973, 2936, 2877, 1746, 1705, 1511, 1454, 1367, 1175 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.12-7.03 (m, 2H), 6.87-6.77 (m, 2H), 5.04-4.67 (m, 2H), 4.21-4.09 (m, 1H), 3.78 (s, 3H), 3.71 (dtd, J=8.6, 6.8, 1.9 Hz, 1H), 3.50 (dtd, J=8.4, 6.6, 1.7 Hz, 1H), 3.34-3.25 (m, 3H), 3.12 (td, J=9.3, 3.6 Hz, 1H), 3.07-2.98 (m, 1H), 2.27 (ddd, J=13.4, 11.7, 6.2 Hz, 1H), 2.07 (s, 2H), 1.76 (s, 1H), 1.71-1.54 (m, 4H), 1.55-1.33 (m, 14H), 0.97 (td, J=7.4, 1.0 Hz, 3H), 0.81 (s, 1H); 13C NMR (101 MHz, CDCl3) δ 173.30, 157.80, 132.75, 129.69, 113.73, 99.98, 84.02, 83.99, 81.11, 75.59, 75.52, 55.25, 55.23, 46.20, 35.86, 35.82, 28.32, 26.56, 23.59, 19.21, 18.19, 18.12, 10.75; HRMS-ESI (m/z) ([M]+) calcd for C27H43NO7, 493.3040; found, 493.3018.

Workup

  1. customThe vial was evacuated
  2. filtrationThe reaction mixture was filtered through a plug of Celite®
  3. concentrationconcentrated to the title compound as a colorless oil (168 mg, 84%) IR (neat) 3368, 2973, 2936, 2877, 1746, 1705, 1511, 1454, 1367, 1175 cm−1

Sources & evidence

ORD record
ord-27e5c7b3ceb549c8b342354003e2ff85
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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