Hydrochloric Acid → 2-{4-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-phenoxy}-2-methyl-propionic acid ethyl ester

HRID 852397Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[H-].[Na+].[CH3:27]I.Cl>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:27])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cooled and stirred solution of 4.0 g (12 mmol) of the above prepared 2-[4-(tert-butoxycarbonylamino-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester in 37 ml DMF was cooled (0° C.), and treated with 0.78 g (55% in oil, 18 mmol) of sodium hydride and, after 30 min, with 5.93 ml (95 mmol) of CH3I. The reaction was stirred at 0° C. to room temperature for 16 h. Subsequently, the solution was poured onto ice water, adjusted to pH 1 (with aqueous 1N HCl) and extracted with ether (two times). The organic layers were washed with water, dried (MgSO4), evaporated and purified by flash chromatography (SiO2, heptane/AcOEt=9:1) to finally give 3.68 g of the title compound as colorless oil.

Workup

stirringThe reaction was stirred at 0° C. to room temperature for 16 h
additionSubsequently, the solution was poured onto ice water
extractionextracted with ether (two times)
washThe organic layers were washed with water
dry with materialdried (MgSO4)
customevaporated
custompurified by flash chromatography (SiO2, heptane/AcOEt=9:1) to finally give 3.68 g of the title compound as colorless oil

Sources & evidence

ORD record: ord-37961c52ba594f7cbf5b421596fcee23
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253192B2

Reaction notes

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