Ethanolamine → L-Isoleucine

HRID 2293397Notes

Reaction equation

HRID 2293397 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].NCCO>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 700EthanolamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 6306L-IsoleucineYield 166.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (0.215 g, 0.58 mmol, 1.0 eq), and triethylamine (96 uL, 70 mg, 0.64 mmol, 1.20 eq), in acetonitrile (10 mL) was treated with isobutyl chloroformate (83 uL, 86 mg, 0.63 mmol, 1.1 eq) followed by 2-aminoethanol (69 uL, 70 mg, 1.15 mmol, 2.0 eq). Workup as above provided 127 mg (53%) of L-isoleucine, N-[1-(2-(2-hydroxyethylamine)-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-1f5ee7c962dd4b7fb375ee724ef012a9
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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