1-Phenylpiperazine → L-Isoleucine

HRID 2293398Notes

Reaction equation

HRID 2293398 reaction equation
C(CN1CCC[C@H]1C(N(CC1C=CC=CC=1)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=O)(O)=O.C(N(CC)CC)C.ClC(OCC(C)C)=[O:37].C1(N2CCNCC2)C=CC=CC=1>C(#N)C>[NH2:12][C@H:11]([C:10]([OH:17])=[O:37])[C@H:13]([CH2:15][CH3:16])[CH3:14]

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 6306L-IsoleucineYield 223.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (0.214 g, 0.58 mmol, 1.0 eq), and triethylamine (96 uL, 70 mg, 0.64 mol, 1.20 eq), in acetonitrile (6 mL) was treated with isobutyl chloroformate (83 uL, 86 mg, 0.63 mmol, 1.1 eq) followed by 4-phenylpiperazine (170 uL, 186 mg, 1.15 mmol, 2.0 eq). Workup as above provided 170 mg (57%) of L-isoleucine, N-[1-[2-(4-phenylpiperazine)-2-oxoethyl]-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-2129e019e0b847fbaa45d1ddf8677a75
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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