DCCI HOBt → Decylamine
Reaction equation
C1CCC(N=C=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)CC1.[CH:16]1[CH:17]=CC2N(O)N=N[C:20]=2[CH:21]=1>CO>[CH3:17][CH2:16][CH2:21][CH2:20][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:10][NH2:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Equation 2 shows the synthetic steps involved in the construction of the required N-[p methyl-aminobenzoyl]-glutamyl-γ-4-fluoroglutamic acid (12). The free acid 7 was obtained by treatment with Dowex 50WX8 in 60% EtOH/H2O. Coupling of the α, γ-carboxyl protected D,L-erythro, threo-4-fluoroglutamate ester to 8 was accomplished using DCC/HOBt giving the pipeptide 9 in 90% yield, hydrogenation of 9 in MeOH using 10% Pd on carbon catalyst gave the free amine 10 in quantitative yield.
Sources & evidence
- ORD record
- ord-df5b0e3cb19b4005afbb00c7b466dcda
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628090
Reaction notes
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