Piperidine → 3-(4-Formylbenzamido)propanoic acid

HRID 1633967Notes

Reaction equation

HRID 1633967 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].C1C=CC2N(O)N=NC=2C=1.C(N=C=NC(C)C)(C)C>CN(C=O)C.C(#N)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

8

Reactant 5

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanine

Product 1

HCID 225023533-(4-Formylbenzamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To the above resin bound Fmoc β-alanine was added 500 μL of a 20% solution of piperidine in DMF. After 30 min of shaking, 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 200 μmol HOBt (31 mg) dissolved in DMF (500 μL) were added to the resin followed by 200 μmol diisopropyl carbodiimide (DIC, 25.2 mg) dissolved in acetonitrile (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).

Workup

  1. washwashed with 1 mL DMF
  2. additioncontaining 1-hydroxybenzotriazole (50 mg/mL) and DMF (2×1 mL)
  3. additionwere added to the resin
  4. stirringThe mixture was shaken for 4 hours at 25° C.
  5. filtrationfollowed by filtration
  6. washwashing of the resin with DMF (3×1 mL)

Sources & evidence

ORD record
ord-218ab136e79a46d3bd88ab9f7fe60792
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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