Water → HCID 69241992, compound

HRID 2242183Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:26][N:27](C=O)C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:26]#[N:27])[CH2:10][C@H:9]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of Example 17B (16.55 g, 44 mmol) in dry DMF (100 mL) under nitrogen was added tetrabutylammonium cyanide (50 g, 200 mmol). The mixture was heated to 50° C. for 60 hours and then poured into cold water and extracted with ethyl acetate (3×250 mL). The combined organic layers were dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane to provide the titled compound (12 g). MS (ESI) m/e 312 (M+H)+, 310 (M−H)−; 1H NMR (400 MHz, CD3OD) δ ppm 1.44 (m, 9 H) 2.10 (m, 1 H) 2.79 (m, 1 H) 3.05 (m, 1 H) 3.17 (m, 1 H) 3.33 (m, 1 H) 3.57 (dd, 1 H) 3.83 (m, 2 H) 3.96 (m, 1 H) 4.48 (m, 1 H) 4.65 (m, 2 H).

Workup

extractionextracted with ethyl acetate (3×250 mL)
dry with materialThe combined organic layers were dried (magnesium sulfate)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane

Sources & evidence

ORD record: ord-7bcdc443f6b7411cbbb995defc7f1f35
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671076B2

Reaction notes

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