Hydrochloric Acid → 4-{3,5-Dichloro-4-[1-(4-hydroxy-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-phenoxy}-benzoic acid methyl ester

HRID 2235318Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][CH:19]3[CH2:23][CH2:22][N:21]([C@H:24]4[CH2:29][CH2:28][C@@H:27]([O:30][Si](C(C)(C)C)(C)C)[CH2:26][CH2:25]4)[C:20]3=[O:38])=[C:13]([Cl:39])[CH:12]=2)=[CH:6][CH:5]=1.Cl>CCO>[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]([Cl:39])[C:14]([CH2:18][CH:19]3[CH2:23][CH2:22][N:21]([CH:24]4[CH2:25][CH2:26][CH:27]([OH:30])[CH2:28][CH2:29]4)[C:20]3=[O:38])=[C:15]([Cl:17])[CH:16]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Dissolve 90 mg of 4-(4-{1-[cis-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-2-oxo-pyrrolidin-3-ylmethyl}-3,5-dichloro-phenoxy)-benzoic acid methy ester (Preparation 73) in 10 mL EtOH and treat with 1 mL 1 N aqueous HCl. Heat at 60° C. for 2 hours. Concentrate to dryness under vacuum and purify by radial chromatography using 5% MeOH in CHCl3 to recover 73 mg of product. Mass spectrum (api-es) m/z 492 (M+H).

Workup

concentrationConcentrate to dryness under vacuum
custompurify by radial chromatography
customto recover 73 mg of product

Sources & evidence

ORD record: ord-1345527332af464d9d77288e324771e0
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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