Piperidine → 3-(4-Formylbenzamido)propanoic acid
Reaction equation
C([NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N1CCCCC1.[CH:30]([C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=O)=[CH:34][CH:33]=1)=[O:31].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:30]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:38])=[CH:39][CH:40]=1)=[O:31]Participants
7
Procedure
To the above resin bound Fmoc β-alanine was added 1000 μL of a 20% solution of piperidine in DMF. Upon shaking for 30 min, the resin was drained and washed with 1 mL DMF containing 1-hydroxybenzotriazole (50 mg/mL) and DMF (2×1 mL). Then 200 μmol 4-formylbenzoic acid (30 mg) and diisopropylethylamine (70 μL) were dissolved in DMF (430 μL) and added to the resin followed by 200 μmol PyBrOP dissolved in DMF (500 μL). The mixture was shaken for 4 hours at 25° C. followed by filtration and washing of the resin with DMF (3×1 mL) and trimethylorthoformate (1×1 mL).
Workup
- washwashed with 1 mL DMF
- additioncontaining 1-hydroxybenzotriazole (50 mg/mL) and DMF (2×1 mL)
- additionadded to the resin
- stirringThe mixture was shaken for 4 hours at 25° C.
- filtrationfollowed by filtration
- washwashing of the resin with DMF (3×1 mL) and trimethylorthoformate (1×1 mL)
Sources & evidence
- ORD record
- ord-82088f74e645486c893ed04e94018374
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06503949B1
Reaction notes
Loading…