Piperidine → Beta-Alanine

HRID 232512Notes

Reaction equation

HRID 232512 reaction equation
[C:1]([NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.N1CCCCC1>CN(C=O)C>[NH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].[C:1]([NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanineHCID 131719749PyBOP HOBt NMM

Product 2

HCID 239Beta-AlanineHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Optionally a gel film plate of the type in Example 3 may have a tetrapeptide spacer attached to the substrate. A plate prepared as in Example 3 had Fmoc-beta-alanine (BAla) coupled to it (standard PyBOP+HOBt/NMM procedure, 2 hours). Following thorough DMF washes, the plate was treated with 30% piperidine in DMF (1, 45 minutes). The plate was washed 2 times with DMF, and the piperidine treatments and subsequent washes were pooled and read spectrophotometrically at 301 nm to determine the Fmoc-loading (in this example 2 micromoles per substrate area). Three more coupling cycles were then performed adding Fmoc-epsilon-aminocaproic acid twice, then beta-alanine again to give the final BAla-Aca-BAla spacer arm film plate as used in the preferred embodiment for ASBCL or ASPCL libraries.

Workup

  1. customA plate prepared as in Example 3
  2. washThe plate was washed 2 times with DMF
  3. additionThree more coupling cycles were then performed adding Fmoc-epsilon-aminocaproic acid twice

Sources & evidence

ORD record
ord-3e76192d9e7c4a60a4c0a530547b1e5a
Source dataset
uspto-grants-1997_01
Patent number
US05591646

Reaction notes

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