3-Carboxybenzaldehyde → 3-Hydroxy-2,2-dimethylbutanoic acid
Reaction equation
BrC1[CH:3]=[C:4]([CH:7]=[CH:8]C=1F)[CH2:5]N.C(C1C=C(C=CC=1)[C:16]([OH:18])=[O:17])=O.CC(C)N=C=NC(C)C.ClCCCl.CN(C=[O:39])C>>[CH3:8][CH:7]([OH:39])[C:4]([C:16]([OH:18])=[O:17])([CH3:5])[CH3:3]Participants
5
Procedure
To a mixture of above resin-bound 3-bromo-4-fluoro-benzylamine (200 mg, 1.15 mmol/g (theoretical loading), 0.23 mmol) in DCE/DMF (1:1, 8 mL) was added 3-formylbenzoic acid (350 mg, 2.3 mmol) and DIC (0.36 mL, 2.3 mmol). The mixture was shaken at rt for overnight and was then washed with DMF (20 mL×2), DCM (20 mL×2), MeOH (20 mL×2) and DCM (20 mL×2). The resulting resin was dried in vacuum oven at 20° C. for overnight to yield DMHB resin-bound N-[(3-bromo-4-fluorophenyl)methyl]-3-formylbenzamide (0.23 mmol). An analytical amount of the resin was cleaved with 50% of TFA in DCE for 10 min. The resulting solution was concentrated in vacuo and dissolved in 0.5 mL of CH3CN. MS (ESI): 336 [M+H]+.
Workup
- washwas then washed with DMF (20 mL×2), DCM (20 mL×2), MeOH (20 mL×2) and DCM (20 mL×2)
- customThe resulting resin was dried in vacuum oven at 20° C. for overnight
Sources & evidence
- ORD record
- ord-7d91d53f86e34493b5c32c99bbecd035
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932247B2
Reaction notes
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