L-Aspartic Acid → Ninhydrin

HRID 850272Notes

Reaction equation

HRID 850272 reaction equation
N[C@H:2]([C:7](O)=O)[CH2:3][C:4](=O)O.N[C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14](=O)[OH:15].CC([O:24]C(N[C@H](C(O)=O)CC(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)=O)(C)C.CC(OC(N[C@H](C(O)=O)CCC(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)=O)(C)C>>[CH:2]1[CH:7]=[C:13]2[C:14]([C:17]([OH:19])([OH:18])[C:11](=[O:24])[C:12]2=[CH:4][CH:3]=1)=[O:15]

Participants

5

Reactant 4

HCID 5960L-Aspartic Acid2×HCID 33032L-Glutamic Acid2×HCID 129966N-alpha-tert-Butyloxycarbonylglutamic acid gamma-fluorenylmethyl esterHCID 164019N-alpha-tert-Butyloxycarbonyl-aspartic acid gamma-fluorenylmethyl ester

Product 1

HCID 10236Ninhydrin

Procedure

This methodology uses Nα -Boc-amino acids together with OFm side-chain protection for Asp and Glu. Asp and Glu were introduced with Boc-Asp(OFm)-OH and Boc-Glu(OFm)-OH. After coupling the last amino acid, the OFm protecting groups were selectively removed by treating the peptide resin in 50% piperidine in DMF (Dimethylformamide) for 1 h. The peptide resin was washed with DMF (3×40 mL), DCM (dicholoromethane) (3×40 mL), suspended in 15 mL of DMF, and mixed with a 6-fold excess of BOP reagent in the presence of an 8-fold excess of diisopropylamine (DIEA) for 5 h. The coupling was repeated until the resin gave the negative ninhydrin test.

Workup

  1. customwere selectively removed
  2. additionby treating the peptide resin in 50% piperidine in DMF (Dimethylformamide) for 1 h
  3. washThe peptide resin was washed with DMF (3×40 mL), DCM (dicholoromethane) (3×40 mL)
  4. additionmixed with a 6-fold excess of BOP reagent in the presence of an 8-fold excess of diisopropylamine (DIEA) for 5 h

Sources & evidence

ORD record
ord-f994617829bf4f45b55582893ddba8c3
Source dataset
uspto-grants-2000_01
Patent number
US06017877

Reaction notes

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