Dicyclohexylcarbodiimide → HCID 131720294, compound

HRID 2293408Notes

Reaction equation

HRID 2293408 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.[CH3:43][CH:44]([CH3:53])[C@@H:45]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)O>ClCCl>[CH3:43][CH:44]([CH3:53])[C@@H:45]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[O:2][C:1](=[O:3])[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]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5325937(S)-(-)-2-Methyl-1-phenyl-1-propanolHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720294HCID 131720294, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the procedure described previously, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (298 mg, 0.73 mmol), 4-N,N-dimethylaminopyridine (95 mg, 0.77 mmol, 1.2 eq), 1,3-dicyclohexylcarbodiimide (243 mg, 1.18 mmol, 1.8 eq) in dichloromethane (10 mL) was treated with (S)-2-methyl-1-phenyl-1-propanol (100 mg, 0.64 mmol, 1.3 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 104 mg (32%) of L-isoleucine, N-[1-(2-(2-methyl-1-(S)-phenyl-1-propoxy)-2-oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-aff3061173844f46b53714325535b9ab
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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