Dicyclohexylcarbodiimide → HCID 131720288, compound

HRID 2293403Notes

Reaction equation

HRID 2293403 reaction equation
[C:1]([CH2:4][N:5]1[CH2:27][CH2:26][CH2:25][C@H:6]1[C:7]([N:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])([OH:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:43](O)/[CH:44]=[CH:45]/[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>ClCCl>[C:46]1([CH:45]=[CH:44][CH2:43][O:2][C:1](=[O:3])[CH2:4][N:5]2[CH2:27][CH2:26][CH2:25][C@H:6]2[C:7]([N:9]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5315892Cinnamyl AlcoholHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720288HCID 131720288, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the procedure described previously, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (65 mg, 0.17 mmol), 4-N,N-dimethylaminopyridine (12.5 mg, 0.10 mmol, 0.6 eq), 1,3-dicyclohexylcarbodiimide (64 mg, 0.31 mmol, 1.8 eq) in dichloromethane (5.0 mL) was treated with trans cinnamyl alcohol (29 uL, 0.22 mmol, 1.3 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 32 mg (38%) of L-isoleucine, N-[1-(2-(3-phenyl-2-propen-1-oxy)-2 -oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-e4b29e130fac41838a36f9a993c76796
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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