Sodium hydride → HCID 68427417, compound

HRID 642291Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:18]Br)=[O:5])[CH3:2].[CH2:20]([O:22][C:23](=[O:33])[CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:21].[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:18][N:25]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:33])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-bromomethyl-2-(4-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (2.22 g, 6.18 mmol), tert-butoxycarbonylamino-acetic acid ethyl ester (1.32 g, 6.48 mmol) and sodium hydride (60% in mineral oil, 296 mg, 7.4 mmol) in anhydrous dimethylformamide (30 mL) was stirred at 0° C. for one hour and room temperature for four hours before it was quenched with brine. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow oil (964 mg): 1H NMR (CDCl3, 200 MHz): δ=7.87 (d, 2H), 7.39 (d, 2H), 4.99 (m, 2H), 4.21 (m, 6H), 1.45 (s, 9H), 1.26 (t, 3H).

Workup

customwas quenched with brine
customThe mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with water, brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record: ord-843de80454ca4fa3923b552e7a005a17
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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