tert-Butanol → HCID 86701265, compound

HRID 2276065Notes

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]([OH:22])=[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].[C:31](O)([CH3:34])([CH3:33])[CH3:32].C(=NC(C)C)=NC(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:24]([O:23][C@@H:13]1[C@@H:14]([CH2:19][C:20]([O:22][C:31]([CH3:34])([CH3:33])[CH3:32])=[O: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]([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 0 °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 (400 mg, 0.928 mmol) in CH2Cl2 (2 mL) was added tert-butyl alcohol (3.44 mg, 4.64 mmol) and DMAP (91 mg, 0.744 mmol) at room temperature (about 22° C.). The solution was cooled to 0° C. and N,N′-methanediylidenedipropan-2-amine (172 uL, 1.11 mmol) was added. The reaction mixture was warmed to room temperature, stirred for 2 h, and then loaded directly onto a SiO2 column and purified by flash chromatography (hexanes/EtOAc gradient) to give the title compound (380 mg, 84%) as a white solid: mp 170-172° C.; 1H NMR (400 MHz, CDCl3) δ 5.44-5.15 (m, 2H), 5.08-4.94 (m, 1H), 4.93-4.75 (m, 2H), 3.74-3.54 (m, 1H), 2.98-2.87 (m, 1H), 2.83-2.71 (m, 1H), 2.61 (hept, J=7.0 Hz, 1H), 2.32-2.21 (m, 1H), 1.44 (s, 9H), 1.40 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.21 (dd, J=7.0, 1.6 Hz, 6H); ESIMS m/z 410 ([M+Na]+).

Workup

temperatureThe reaction mixture was warmed to room temperature
custompurified by flash chromatography (hexanes/EtOAc gradient)

Sources & evidence

ORD record: ord-8e5f88b9a6e4454eb5c3648c7a9ce404
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09131690B2

Reaction notes

Loading…