HCID 86701321, compound → HCID 86701322, compound

HRID 2283014Notes

Reaction equation

HRID 2283014 reaction equation
[C:1]([O:5][C:6]([N:8]([C@H:16]1[CH2:24][O:23][CH2:22][C@H:21]([O:25][CH2:26][CH:27]=[CH2:28])[C@@H:20]([O:29][CH2:30][CH:31]=[CH2:32])[C@H:19]([CH3:33])[O:18][C:17]1=[O:34])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]([C@H:16]1[CH2:24][O:23][CH2:22][C@H:21]([O:25][CH2:26][CH2:27][CH3:28])[C@@H:20]([O:29][CH2:30][CH2:31][CH3:32])[C@H:19]([CH3:33])[O:18][C:17]1=[O:34])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86701321HCID 86701321, compound

Product 1

HCID 86701322HCID 86701322, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[(3S,7S,8S,9S)-7,8-diallyloxy-9-methyl-2-oxo-1,5-dioxonan-3-yl]carbamate (170 mg, 0.350 mmol) in EtOAc (3 mL) in a 50 mL high pressure reactor with a stir bar was added 5% Pd/C (20.0 mg, 9.40 μmol). After the reactor was sealed, it was purged with H2 (4×), and charged to ˜600 psi with H2 at room temperature. The reaction mixture was warmed to 40° C. and stirred for 2 h. The reaction mixture was filtered through a pad of Celite® and the filtrate concentrated to provide the title compound as a colorless oil (170 mg, 99%): 1H NMR (400 MHz, CDCl3) δ 5.21 (dd, J=8.9, 4.2 Hz, 1H), 4.77 (dq, J=9.3, 6.2 Hz, 1H), 4.26 (dd, J=12.1, 4.2 Hz, 1H), 3.92 (dd, J=12.1, 8.9 Hz, 1H), 3.86-3.77 (m, 2H), 3.60-3.41 (m, 4H), 3.29-3.12 (m, 2H), 1.67-1.52 (m, 2H), 1.49 (s, 19H), 1.42 (d, J=6.4 Hz, 3H), 0.92 (td, J=7.4, 2.8 Hz, 7H); 13C NMR (101 MHz, CDCl3) δ 169.04, 152.59, 84.88, 83.40, 82.95, 75.71, 75.41, 72.78, 72.65, 72.55, 57.88, 27.91, 23.48, 23.27, 18.62, 10.59, 10.57; ESIMS m/z 513.3 ([M+Na]+).

Workup

  1. customAfter the reactor was sealed
  2. customit was purged with H2 (4×)
  3. additioncharged to ˜600 psi with H2 at room temperature
  4. filtrationThe reaction mixture was filtered through a pad of Celite®
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-64688503982f474791b4f00681e0444c
Source dataset
uspto-grants-2015_09
Patent number
US09144239B2

Reaction notes

Loading…