Benzoyl chloride → HCID 11163527, compound

HRID 2296932Notes

Reaction equation

HRID 2296932 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.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[C:27]([NH:1][C:2]1[CH:3]=[CH:4][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:6][CH:7]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 11436223HCID 11436223, compound

Product 1

HCID 11163527HCID 11163527, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-amino-phenyl)-3-cyclopentyl-propionic acid (49 mg, 0.21 mmol) in tetrahydrofuran (5 mL) was treated with N,N-diisopropylethylamine (0.04 mL, 0.25 mmol) and benzoyl chloride (0.02 mL, 0.21 mmol). The reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) afforded 2-(4-benzoylamino-phenyl)-3-cyclopentyl-propionic acid (41 mg, 57.9%) as a white solid: mp 192.5-194° C.; EI-HRMS m/e calcd for C21H23NO3 (M+) 337.1677, found 337.1670.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-85560e7d11894ef2b0a062387a98917f
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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