Triethylamine → HCID 131720293, compound

HRID 2293407Notes

Reaction equation

HRID 2293407 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])(O)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:43]12([CH2:53][NH2:54])[CH2:52][CH:47]3[CH2:48][CH:49]([CH2:51][CH:45]([CH2:46]3)[CH2:44]1)[CH2:50]2>C(#N)C>[C:43]12([CH2:53][NH:54][C:1]([CH2:4][N:5]3[CH2:27][CH2:26][CH2:25][C@H:6]3[C:7]([N:9]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])=[O:2])[CH2:50][CH:49]3[CH2:48][CH:47]([CH2:46][CH:45]([CH2:51]3)[CH2:44]1)[CH2:52]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720293HCID 131720293, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described previously, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (106 mg, 0.28 mmol), triethylamine (158 uL, 1.13 mmol, 4 eq) in acetonitrile (1.5 mL, was cooled to 0° C. and treated with isobutyl chloroformate (40.5 uL, 0.31 mmol, 1.1 eq) followed by 1-adamantanemethylamine (100 uL, 0.57 mmol, 2 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 15 mg (10%) of L-isoleucine, N-[1-(adamant-1-ylmethylcarbamoylmethyl)-L-prolyl] benzylamide.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-7e927f8c87bd4ccdaefecc6d3c3a2896
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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