HCID 86701297, compound → HCID 86701298, compound

HRID 2282999Notes

Reaction equation

[CH3:1][C@@H:2]1[O:10][C:9](=[O:11])[C@@H:8]([NH:12]C(=O)OCC2C=CC=CC=2)[CH2:7][O:6][CH2:5][C@H:4]([O:23][CH2:24][C:25]([CH3:27])=[CH2:26])[C@H:3]1[O:28][CH2:29][C:30]([CH3:32])=[CH2:31]>CCOC(C)=O.[Pd]>[NH2:12][C@H:8]1[CH2:7][O:6][CH2:5][C@H:4]([O:23][CH2:24][CH:25]([CH3:26])[CH3:27])[C@@H:3]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C@H:2]([CH3:1])[O:10][C:9]1=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

Benzyl (3S,7S,8S,9S)-9-methyl-7,8-bis(2-methylallyloxy)-2-oxo-1,5-dioxonan-3-ylcarbamate (265 mg, 0.592 mmol) was dissolved in EtOAc (8 mL) in a 50 mL high pressure reactor with a stir bar and Pd/C (5%, 30 mg) was added. The reactor was sealed and purged with H2 (4×), then charged to ˜600 pounds per square inch (psi) with H2. The reactor was warmed to 50° C. and stirred at 50° C. for 12 h. The reaction mixture was filtered through a pad of Celite® and the filtrate was concentrated to afford the title compound as a white solid (170 mg, 91%): mp 144-146° C.; 1H NMR (400 MHz, CDCl3) δ 4.82 (dq, J=8.5, 6.3 Hz, 1H), 3.97-3.84 (m, 1H), 3.78 (t, J=7.0 Hz, 1H), 3.72-3.53 (m, 3H), 3.44-3.29 (m, 2H), 3.29-3.12 (m, 4H), 1.82 (ttd, J=13.4, 6.5, 2.5 Hz, 2H), 1.42 (d, J=6.3 Hz, 3H), 0.99-0.78 (m, 12H); 13C NMR (101 MHz, CDCl3) δ 175.66, 84.70, 83.85, 80.55, 77.57, 74.90, 72.72, 72.70, 29.11, 28.87, 19.58, 19.48, 19.45, 19.38, 18.61; ESIMS m/z 318.8 ([M+H]+).

Workup

customThe reactor was sealed
custompurged with H2 (4×)
additioncharged to ˜600 pounds per square inch (psi) with H2
filtrationThe reaction mixture was filtered through a pad of Celite®
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-d1290686a9134d41a636e467cce2bc46
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09144239B2

Reaction notes

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