4-Methylmorpholine → 5-Methylisoxazole-4-carboxylic acid

HRID 432017Notes

Reaction equation

NC1[O:3][C:4]2[CH:10]=CC=CC=2N=1.CN1C[CH2:16][O:15]CC1.C1C[O:21]CC1.[C:23](#[N:25])[CH3:24]>>[CH3:10][C:4]1[O:3][N:25]=[CH:23][C:24]=1[C:16]([OH:15])=[O:21]

Participants

Reactant 3

HCID 79724-Methylmorpholine

HCID 207072-Aminobenzoxazole

HCID 22177404Acetonitrile tetrahydrofuran

Product 1

HCID 14252405-Methylisoxazole-4-carboxylic acid

Procedure

Sulfonylation (X═SO2) For 45 μmol of aminobenzoxazole resin in each well of a 96-well microtiter plate, 1 mL RSO2Cl/THF-ACN /NMM/NMI (0.3M, 0.3 mmol RSO2Cl; 20% THF-ACN (by volume); 0.6M, 0.6 mmol NMM; 0.1M, 0.1 mmol NMI) was added to each well. The sulfonyl chlorides (RSO2Cl) used were as follows:

Sources & evidence

ORD record: ord-dd31873a1292414294ef4b7a133d933b
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660858B2

Reaction notes

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