HCID 69686698, compound → HCID 53762810, compound

HRID 2231090Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH2:12][CH2:11][C:10](=O)[NH:9]1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH2:12][CH2:11][CH2:10][NH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,7-dioxo-[1,2]diazepan-1-yl]-acetic acid tert-butyl ester (4) (775 mg, 2.0 mmol) in THF (4 mL) was added borane-THF complex in THF (1M, 4 mL). The reaction was stirred at 0° C. for 30 min then at room temperature for 3 hours. The mixture was diluted with ice-water (60 mL), extracted with ethyl acetate (60 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a solid, that was purified by flash chromatography using hexane/ethyl acetate (95/5 to 70/30) to afford 585 mg (78% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.43 (s, 9H), 1.78-1.90 (m, 1H), 2.00-2.15 (m, 2H), 2.65-2.78 (m, 1H), 2.95-3.07 (m, 1H), 3.22-3.30 (m, 1H), 3.85-3.92 (d, 1H), 4.30-4.42 (m, 2H), 5.39-5.42 (m, 1H), 7.62-7.71 (m, 2H), 7.79-7.86 (m, 2H). Analytical HPLC: 7.86 min. LC-MS (ES+): m/e=374 (M+H+).

Workup

waitat room temperature for 3 hours
extractionextracted with ethyl acetate (60 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
customevaporated in vacuo
customto give a solid, that
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-effb1e57629d49d28a035c0010d8487f
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06426413B1

Reaction notes

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