1-Phenyl-1-propanol → HCID 131720290, compound

HRID 2293404Notes

Reaction equation

HRID 2293404 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.[C:43]1([CH:49](O)[CH2:50][CH3:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl>[C:43]1([CH:49]([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])[CH2:50][CH3:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 71471-Phenyl-1-propanolHCID 10868DicyclohexylcarbodiimideHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720290HCID 131720290, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (59 mg, 0.16 mmol), 4-N,N-dimethylaminopyridine (7.9 mg, 0.06 mmol, 0.4 eq), 1,3-dicyclohexylcarbodiimide (49 mg, 0.23 mmol, 1.5 eq) in dichloromethane (5.0 mL) was treated with (±) 1-phenyl-1-propanol (28 uL, 0.20 mmol, 1.3 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 32 mg (41%) of L-isoleucine, N-[1-(2-(1-phenylpropoxy)-2-oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-dd983771c74d41e79db1b40b7ccb6bf4
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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