Reaction #79445

ord-3adcf0f3a9694e53b5a862322e9894d9

Reaction equation

O=C(Cl)c1ccc(Cl)c(Cl)c1
3,4-dichlorobenzoyl chloride
O=C(N[C@@H](Cc1c[nH]cn1)C(=O)O)OCC1c2ccccc2-c2ccccc21
Fmoc-L-histidine
CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-L-leucine
O=Cc1cccs1
thiophene-2-carboxaldehyde
→
O=C(O)C1CC(Cc2c[nH]cn2)(C(=O)O)N(C(=O)c2ccc(Cl)cc2)C1c1ccco1
title compound
O=C(O)C1CC(Cc2c[nH]cn2)(C(=O)O)N(C(=O)c2ccc(Cl)cc2)C1c1ccco1
1-[1-(4-Chloro-phenyl)-methanoyl]-5-furan-2-yl-2-(1H-imidazol-4-ylmethyl)-pyrrolidine-2,4-dicarboxylic Acid

Reactants

O=C(Cl)c1ccc(Cl)c(Cl)c1
3,4-dichlorobenzoyl chloride
O=C(N[C@@H](Cc1c[nH]cn1)C(=O)O)OCC1c2ccccc2-c2ccccc21
Fmoc-L-histidine
CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-L-leucine
O=Cc1cccs1
thiophene-2-carboxaldehyde

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following the procedure of Example 28(a)-28(d), except beginning with Wang bound Fmoc-L-histidine (Trt) instead of Wang bound Fmoc-L-leucine, and substituting furan-2-carboxaldehyde for thiophene-2-carboxaldehyde, and substituting 4-chlorobenzoylchloride for 3,4-dichlorobenzoyl chloride, the title compound was prepared as a solid. MS [M+H]+444.8

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713502B2uspto-grants-2004_03