Dicyclohexylcarbodiimide → HCID 131720291, compound

HRID 2293405Notes

Reaction equation

HRID 2293405 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.[CH:43]1([CH:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)O)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>ClCCl>[C:43]1([CH:49]([CH:51]2[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]2)[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:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 95668Cyclohexyl(phenyl)methanolHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720291HCID 131720291, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the procedure described previously, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (71 mg, 0.19 mmol), 4-N,N-dimethylaminopyridine (7.5 mg, 0.06 mmol, 0.3 eq), 1,3-dicyclohexylcarbodiimide (64 mg, 0.31 mmol, 1.6 eq) in dichloromethane (5.0 mL) was treated with (±) cyclohexylphenylcarbinol (45 mg, 0.24 mmol, 1.3 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 27 mg (26%) of L-isoleucine, N-[1-(2-(1-phenyl-1-cyclohexylmethoxy)-2-oxoethyl)-L-prolyl] benzylamide (RD-08-71, Z6338).

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-c2362031750f489bb3b83e9679d44c97
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

Loading…