Water → HCID 131724644, compound

HRID 2415044Notes

Reaction equation

[Li]CCCC.[CH2:6]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:15]=2)[C:10]1=[O:22])[CH2:7][CH3:8].[CH3:23][C:24]([O:27][C:28](/[N:30]=[N:31]/[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:29])([CH3:26])[CH3:25].O>O1CCCC1>[CH3:26][C:24]([O:27][C:28]([NH:30][N:31]([C:9]1([CH2:6][CH2:7][CH3:8])[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:15]=2)[C:10]1=[O:22])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:29])([CH3:23])[CH3:25]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of diisopropropylamine (1.3 mL, 9.1 mmol) in 30 mL tetrahydrofuran cooled to −78° C. was added 6.0 mL n-BuLi (1.6M, 9.5 mmol). The mixture was allowed to warm to −20° C. over 20 min, then re-cooled to −78° C. A solution of the product from Step C (2.0 g, 8.3 mmol) in 15 mL tetrahydrofuran was added dropwise. After 30 min, a solution of di-tert-butylazodicarboxylate (2.1 g, 9.1 mmol) in 20 mL tetrahydrofuran was added dropwise. The reaction was allowed to slowly warm to RT and stirred overnight. Water was added and the mixture was extracted with ethyl acetate, dried (MgSO4), filtered and concentrated. The residue was purified by chromatography on silica gel eluting with 10% ethyl acetate/hexane to afford 2.92 g of a white solid, m.p. 135-137° C.

Workup

temperaturere-cooled to −78° C
temperatureto slowly warm to RT
extractionthe mixture was extracted with ethyl acetate
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record: ord-d15b9f8395b243bba54776d3e52226fd
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818641B2

Reaction notes

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