Diisopropylethylamine → HCID 18388776, compound

HRID 2296948Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1>O1CCCC1>[CH:13]1([CH2:12][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:28]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[O:35])=[CH:7][CH:6]=2)[C:9]([OH:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(4-amino-phenyl)-3-cyclopentyl-propionic acid (130 mg, 0.56 mmol) in tetrahydrofuran (10 mL) at 25° C. was treated with N,N-diisopropylethylamine (0.23 mL, 1.34 mmol) and nicotinoyl chloride hydrochloride (99 mg, 0.54 mmol). The reaction mixture was stirred at 25° C. for 48 h. At this time, the reaction was concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μM, 60 Å, 25 cm×23 cm ID, 90/10 ethyl acetate/heptane) afforded 3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-propionic acid (40.9 mg, 21.7%) as a yellow solid: mp 160-163° C.; EI-HRMS m/e calcd for C21H23NO3 (M+) 337.1677, found 337.1670.

Workup

concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-9c1eb7d964f44917b9ab504b0f7b5172
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489485B2

Reaction notes

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