KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's

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KBS30-7 - N-alkylation with KBS29 #176

Closed KlementineJBS closed 4 months ago

KlementineJBS commented 5 months ago

Link to HIRAC and master page.

KBS30 - Generic alkylation of 1,x-diaminoalkane with naphthalene-triazole pendant (updated).docx

Notes

Using cesium carbonate as base and THF as solvent.

Reaction scheme

KBS30 alternative nosyl protected

KlementineJBS commented 5 months ago

Added 58 mg of SM (0.120 mmol) to a flask
Evacuated and backfilled x 5
Added dry THF (2 mL) and chilled to 0 C
Tried to dissolve KBS29 (77.2 mg, 0.269 mmol, 2.2 equiv.) in dry THF (2 mL) but couldn't get it to dissolve. Ended up transferring contents of flask to the vial containing KBS29 and putting this under nitrogen instead.
Added cesium carbonate (246.5 mg, 0.757 mmol, 6 equiv.).
Left stirring at rt from 3.50 pm

KlementineJBS commented 5 months ago

LRMS

SM, mono product evident. Some mystery peaks.

Mystery 1+ peaks: 602.10, 639.03 Mystery 1- peaks: 566.91

618.93 [M+Cs]+ of SM

KBS30-7 RM 11-01-24.pdf KBS30-7 RM 11-01-24.zip

KlementineJBS commented 5 months ago

12.01.24

Quenched with 10 mL ammonium chloride solution at ~4 pm to maintain consistency.

TLC at time of quenching:

solvent system is 4.5% MeOH, 0.5% ammonium hydroxide in DCM

KlementineJBS commented 5 months ago

Worked up with toluene (3 x 10 mL) and a little DCM, washed with water (30 mL) and brine (30 mL). DCM is an easier solvent to use if multiple washes aren't required (as with DMF) but wanted consistency across these screens.

KlementineJBS commented 5 months ago