Ethylmorpholine → L-Isoleucine

HRID 2293394Notes

Reaction equation

HRID 2293394 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.N1CCCC(C(OCC)=O)C1>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 62365Isobutyl chloroformateHCID 98969Ethyl nipecotateHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 6306L-IsoleucineYield 161.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (266 mg, 0.71 mmol, 1.0 eq), N-ethylmorpholine (135 uL, 1.06 mmol, 1.5 eq) in acetonitrile (5.0 mL) was treated with isobutyl chloroformate (101 uL, 0.78 mmol, 1.1 eq) followed by ethyl nipecotate (220 uL, 1.40 mmol, 2.0 eq). Purification by flash chromatography provided 150 mg (41%) of L-isoleucine, N-[1-[2-[N-(piperidine-3-carboxylic acid ethyl ester)]-2-oxoethyl]-L-prolyl] benzylamide as a colorless oil.

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d895dff602864ad1a1ed52eae549298e
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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