Ethylmorpholine → L-Isoleucine

HRID 2293396Notes

Reaction equation

HRID 2293396 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(N1CC[O:33]CC1)C.ClC(OCC(C)C)=O.CC1CCCCN1>C(#N)C>[NH2:12][C@H:11]([C:10]([OH:17])=[O:33])[C@H:13]([CH2:15][CH3:16])[CH3:14]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 79742-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 6306L-IsoleucineYield 115.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (202 mg, 0.53 mmol, 1.0 eq), N-ethylmorpholine (82 uL, 0.64 mmol, 1.20 eq) in acetonitrile (8 mL) was treated with isobutyl chloroformate (80 uL, 0.62 mmol, 1.15 eq) followed by 2-methylpiperidine (0.106 g, 1.07 mmol, 2.0 eq). The solution was warmed to 22° C., concentrated to a residue, and purified by flash chromatography to provide 80 mg (32%) of L-isoleucine, N-[1-[2-(N-(2-methylpiperidine))-2-oxoethyl]-L-prolyl] benzylamide as a colorless oil.

Workup

  1. concentrationconcentrated to a residue
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-191246fddc3e49438f3f690b4a7735a8
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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