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2nd September 2013 @ 01:26

See also: Coupling of Boc-Gly-OH and 4-aminoantipyrine (PMY 29-2) but with EDCI and HOBt.

Procedure:
Boc-Gly-OH (400 mg, 2.28 mmol, 1 equiv.), EDCI (524 mg, 2.74 mmol, 1.2 equiv.) and HOBt (30 mg, 0.22 mmol, 0.1 equiv.) were stirred in CH2Cl2 (20 mL) and stirred at room temperature for 15 minutes. 4-Aminoantipyrine (510 mg, 2.54 mmol, 1.1 equiv.) was added and the reaction mixture stirred overnight.

A saturated aqueous solution of NaHCO3 was added and the the layers were separated and the aqueous layer was extracted with CH2Cl2. Combined organic layers were washed with water, brine and then dried (MgSO4) to give an orange/brown oil. 

No NMR data recorded - inconclusive result.

Data:

TLC in 10% MeOH in CH2Cl2

Hazard and Risk Assessment:

See Coupling of Boc-Gly-OH and 4-aminoantipyrine (PMY 29-2)

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2nd September 2013 @ 01:18

AEW 81-1 (275 mg, 1.72 mmol, 1 equiv.), EDCI (395 mg, 2.06 mmol, 1.2 equiv.) and HOBt (23 mg, 0.17 mmol, 0.1 equiv.) were stirred in CH2Cl2 (15 mL) and stirred at room temperature for 15 minutes. 4-Aminoantipyrine (238, 1.49 mmol, 1.1 equiv.) was added and the reaction mixture stirred for 16 hours.

A saturated aqueous solution of NaHCO3 was added and the the layers were separated and the aqueous layer was extracted with CH2Cl2. Combined organic layers were washed with water, brine and then dried (MgSO4) to give a red/brown tar that didn't dissolve in NMR solvents.

Reaction abandonded.


Hazard and Risk Assessment

See AEW 64-1

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