Hexane → HCID 68816220, compound

HRID 735230Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](C(C)C(O)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:26][O:27][C:28](=[O:38])[C:29]1[C:34]([Cl:35])=[CH:33][C:32]([Cl:36])=[CH:31][C:30]=1[NH2:37].[CH3:39][CH2:40][CH2:41]CCC.CC[O:47]C(C)=O>>[CH3:26][O:27][C:28](=[O:38])[C:29]1[C:34]([Cl:35])=[CH:33][C:32]([Cl:36])=[CH:31][C:30]=1[NH:37][C:41](=[O:47])[CH:40]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=1)[CH3:39]

Participants

Reactant 5

HCID 8058Hexane

HCID 8857Ethyl Acetate

HCID 24819Phosphorus pentachloride

HCID 12363232Methyl 2-amino-4,6-dichlorobenzoate

HCID 22464929HCID 22464929, compound

Product 1

HCID 68816220HCID 68816220, compoundYield 91%

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-(4-benzyloxy-phenyl)-propionic acid (2.70 g, 10.5 mmol), PCl5 (2.30 g, 10.5 mmol), and 2-amino-4,6-dichloro-benzoic acid methyl ester (1.54 g, 7.0 mmol). After normal workup, the pure objective compound (2.90 g, 91%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.59 (d, J=7.0 Hz, 3H, CH3), 3.65-3.76 (m, 1H, CH), 3.76 (s, 3H, CO2CH3), 5.09 (s, 2H, OCH2Ph), 6.93-6.97 (m, 3H, ArH), 7.14 (d, J=1.8 Hz, 1H, ArH), 7.26-7.48 (m, 6H, ArH), 8.42 (d, J=1.8 Hz, 1H, ArH), 9.02 (s, 1H, NH); MS(EI) m/e 458 [M+], 426, 336, 301, 121, 91.

Sources & evidence

ORD record: ord-2ae01b6aa4a940f1ac87094820af33e5
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592457B2

Reaction notes

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