Reaction #1771999

ord-fc3636fdb60f44aab097345a59cbd981

Reaction equation

C=Cc1ccc(C=C)cc1.C=Cc1ccccc1.Cc1ccc(C(N)c2ccccc2)cc1.Cl
MBHA resin
O=C(N[C@H](C(=O)O)c1ccccc1)OCC1c2ccccc2-c2ccccc21
Fmoc-Phg-OH
C=Cc1ccc(C=C)cc1.C=Cc1ccccc1.Cc1ccc(C(N)c2ccccc2)cc1.Cl.N[C@H](C(=O)O)c1ccccc1
ninhydrin
C=Cc1ccc(C=C)cc1.C=Cc1ccccc1.Cc1ccc(C(N)c2ccccc2)cc1.Cl.N[C@H](C(=O)O)c1ccccc1
H-Phg MBHA Resin

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherequipped with a nitrogen inlet
  2. 2
    WashIt was then washed thoroughly with 30 ml portions of dichloromethane, methanol, dimethylformamide and dichloromethane

Procedure

The commercially available MBHA resin (2.6 g, 1.12 mmol/g, 2.91 mmol) was transferred to a 250 mL fritted solid phase reaction vessel equipped with a nitrogen inlet. It was then washed thoroughly with 30 ml portions of dichloromethane, methanol, dimethylformamide and dichloromethane and coupled over 18 hours to the commercially available Fmoc-Phg-OH (2.17 g, 5.82 mmol) according Procedure A with 99.82% efficiency. The resin was then subjected to Fmoc deprotection according to procedure B. A qualitative ninhydrin assay on a small aliquot gave dark blue resin and solution, indicating a successful reaction.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE043298E1uspto-grants-2012_04