Triethylamine → L-Isoleucine

HRID 2293399Notes

Reaction equation

HRID 2293399 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].N1CCCC1>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 8471TriethylamineHCID 31268PyrrolidineHCID 62365Isobutyl chloroformateHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 6306L-IsoleucineYield 279.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A -5° C. solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (0.212 g, 0.56 mmol, 1.0 eq), and triethylamine (96 uL, 65 mg, 0.65 mmol, 1.15 eq), in acetonitrile (10 mL) was treated with isobutyl chloroformate (77 uL, 80 mg, 0.59 mmol, 1.05 eq) followed by pyrrolidine (94 uL, 80 mg, 1.13 mmol, 2.0 eq). Workup as above provided 205 mg (85%) of L-isoleucine, N-[1-[2-(1-pyrrolidine)-2-oxoethyl]-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-745d89d6d3144c2189f581f6e1c315a1
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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