HCID 86701320, compound → HCID 86701319, compound

HRID 2283012Notes

Reaction equation

HRID 2283012 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]CC2C=CC=CC=2)[C@@H:20]([O:33]CC2C=CC=CC=2)[C@H:19]([CH3:41])[O:18][C:17]1=[O:42])[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:11]([O:10][C:9]([N:8]([C@H:16]1[CH2:24][O:23][CH2:22][C@H:21]([OH:25])[C@@H:20]([OH:33])[C@H:19]([CH3:41])[O:18][C:17]1=[O:42])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 86701320HCID 86701320, compound

Product 1

HCID 86701319HCID 86701319, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[(3S,7S,8S,9S)-7,8-dibenzyloxy-9-methyl-2-oxo-1,5-dioxonan-3-yl]carbamate (3.8 g, 6.49 mmol) in EtOAc (10 mL) in a 50 mL high pressure reactor with a stir bar was added 5% Pd/C (500 mg, 0.235 mmol). After the reactor was sealed, it was evacuated and purged with H2 (4×), and then charged to ˜600 psi of H2 at room temperature. The reaction mixture was warmed to 45° C. and stirred for 5 h. The reaction mixture was filtered through a pad of Celite® and the filtrate concentrated to yield the title compound as a white foam (2.63 g, 100%): 1H NMR (400 MHz, CDCl3) δ 5.25 (dd, J=8.7, 2.8 Hz, 1H), 4.94-4.76 (m, 1H), 4.26 (dd, J=12.3, 2.9 Hz, 1H), 4.06 (dd, J=10.7, 1.3 Hz, 1H), 3.91 (dd, J=12.3, 8.7 Hz, 1H), 3.62-3.54 (m, 1H), 3.54-3.38 (m, 2H), 3.15 (d, J=4.0 Hz, 1H), 2.96 (d, J=3.5 Hz, 1H), 1.51 (s, 18H), 1.46 (d, J=6.3 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 168.63, 152.70, 83.18, 79.34, 77.96, 74.40, 74.25, 73.02, 58.54, 27.98, 18.60; ESIMS m/z 428.5 ([M+Na]+).

Workup

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

Sources & evidence

ORD record
ord-53f948be6528419b91c444f42fdb699e
Source dataset
uspto-grants-2015_09
Patent number
US09144239B2

Reaction notes

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