Borane → HCID 86701260, compound

HRID 2276061Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:17][O:16][C:15](=[O:18])[C@H:14]([CH2:19][C:20](O)=[O:21])[C@@H:13]([O:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[C@H:12]([CH3:29])[O:11][C:10]1=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:24]([O:23][C@@H:13]1[C@@H:14]([CH2:19][CH2:20][OH:21])[C:15](=[O:18])[O:16][CH2:17][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:10](=[O:30])[O:11][C@H:12]1[CH3:29])(=[O:28])[CH:25]([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of 2-((3S,7R,8R,9S)-3-(tert-butoxycarbonylamino)-8-(isobutyryloxy)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)acetic acid (2.0 g, 4.64 mmol) in THF (15 mL) was added borane (1.0 M in THF, 5.56 mL, 5.56 mmol) at 0° C. After 15 min the ice bath was removed and the reaction was allowed to warm to room temperature (about 22° C.). After an additional 1.5 h, the reaction was quenched with EtOAc (10 mL) and washed successively with 0.5 N HCl (10 mL) and sat'd aqueous NaHCO3 (10 mL). The phases were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (1.38 g, 72%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.40-5.19 (m, 2H), 5.07 (t, J=9.9 Hz, 1H), 4.95-4.75 (m, 2H), 3.74-3.52 (m, 3H), 2.83-2.68 (m, 1H), 2.61 (dt, J=13.9, 7.0 Hz, 1H), 2.07-1.90 (m, 1H), 1.70-1.52 (m, 1H), 1.44 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H); ESIMS m/z 440.3 ([M+Na]+).

Workup

customAfter 15 min the ice bath was removed
customthe reaction was quenched with EtOAc (10 mL)
washwashed successively with 0.5 N HCl (10 mL)
customThe phases were separated
dry with materialthe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7cd347e9c76c4d57aea26531d1b3137d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09131690B2

Reaction notes

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