Ninhydrin → 2-Aminobenzophenone

HRID 2364886Notes

Reaction equation

HRID 2364886 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([NH:29]C(OCC2C3CC4C(=CC=CC=4)C=3C=CC=2)=O)=[C:6]([CH:28]=1)[C:7]([C:9]1[CH:27]=[CH:26][C:12](OCC2C=CC(OCC(O)=O)=CC=2)=[CH:11][CH:10]=1)=[O:8].O.OC1C2N=NNC=2C=CC=1.C(N=C=NC(C)C)(C)C.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CN(C=O)C>[NH2:29][C:5]1[CH:4]=[CH:3][CH:2]=[CH:28][C:6]=1[C:7]([C:9]1[CH:27]=[CH:26][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

6

Reactant 4

HCID 10236NinhydrinHCID 12734DiisopropylcarbodiimideHCID 19430039HCID 19430039, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 760802-Aminobenzophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 30 mL peptide reaction flask was added 4-(4-(5-chloro-2-fluorenylmethoxycarbonylamino-benzoyl)-phenoxymethyl)phenoxyacetic acid (1.52 g, 2.4 mmol, 2.0 equivalents), aminomethyl resin (1.99 g, 1.19 mmol of 1% crosslinked divinylbenzene-styrene, 100 mesh size, substitution level 0.60 milliequivalents/g), and hydroxybenzotriazole monohydrate (0.808 g, 5.28 mmol, 4.4 equivalents). Anhydrous DMF (12 mL) was added to the flask and the mixture was vortexed for 0.5 hour to fully solvate the resin. Diisopropylcarbodiimide (808 mg, 5.28 mmol, 4.4 equivalents) was added by syringe. The reaction flask was stoppered and then vortexed for 24 hours at which point the ninhydrin test on approximately 10 mg of the solid support demonstrated that coupling was complete. The solvent and reagents were filtered away from the solid support and the support was rinsed five times with 2.0 mL DMF and five times with 20 mL CH2Cl2 (for each rinse the mixture was vortexed for at least 30 seconds before filtering off the solvent) and then dried in vacuo for 12 hours to give 5.

Workup

  1. waitvortexed for 24 hours at which point
  2. filtrationThe solvent and reagents were filtered away from the solid support
  3. washthe support was rinsed five times with 2.0 mL DMF and five times with 20 mL CH2Cl2 (for
  4. washeach rinse the mixture
  5. waitwas vortexed for at least 30 seconds
  6. filtrationbefore filtering off the solvent) and
  7. customthen dried in vacuo for 12 hours
  8. customto give 5

Sources & evidence

ORD record
ord-83c9e7d6ee2f45cca4bde09aecb0691c
Source dataset
uspto-grants-2014_04
Patent number
US08697032B2

Reaction notes

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