Triethylamine → L-isoleucine, N-[1-(adamantan-2-ylcarbamoylmethyl)-L-prolyl] benzylamide

HRID 2293406Notes

Reaction equation

HRID 2293406 reaction equation
[C:1]([CH2:4][N:5]1[CH2:27][CH2:26][CH2:25][C@H:6]1[C:7]([N:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])([OH:3])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH:43]12[CH2:52][CH:47]3[CH2:48][CH:49]([CH2:51][CH:45]([CH2:46]3)[CH:44]1[NH2:53])[CH2:50]2>C(#N)C>[CH:43]12[CH2:52][CH:47]3[CH2:48][CH:49]([CH2:51][CH:45]([CH2:46]3)[CH:44]1[NH:53][C:1]([CH2:4][N:5]1[CH2:27][CH2:26][CH2:25][C@H:6]1[C:7]([N:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])=[O:3])[CH2:50]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 253322-AminoadamantaneHCID 62365Isobutyl chloroformateHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720292L-isoleucine, N-[1-(adamantan-2-ylcarbamoylmethyl)-L-prolyl] benzylamideYield 6.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described previously, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (113 mg, 0.30 mmol), triethylamine (168 uL, 1.20 mmol, 4 eq) in acetonitrile (1.5 mL, was cooled to 0° C. and treated with isobutyl chloroformate (43 uL, 0.33 mmol, 1.1 eq) followed by the hydrochloride salt of 2-adamantylamine (113.2 mg, 0.60 mmol, 2 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 10 mg (6.5%) of L-isoleucine, N-[1-(adamantan-2-ylcarbamoylmethyl)-L-prolyl] benzylamide.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-c8233a08e60d4eaeb11dc61e24cfbc73
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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