Trimethylsilyl sarcosine

A mixture of sarcosine (45 mg, 0.5 mmol) and bis(trimethylsilyl)acetamide 22a (272 iL, 1.1 mmol) in 0.5 mL acetonitrile is stirred at room temperature for 1 h and at 40 °C for 30 min to give 441, which is then combined with a solution of the glyoxamide 440 in 1 mL abs. toluene. The resulting mixture is heated under reflux for 18 h, cooled, diluted with CHjClj, washed with 1 M NaOH, and the aqueous layer is extracted with CH2CI2. The combined organic layers are washed with brine, dried, concentrated, and purified by chromatography to give 40 mg (40%) 444 as a yellowish oil [49] (Scheme 5.89). 

N-(3-Phenyl-5-trimethylsilyl)-2-penten-4-yne-l-yl)-sarcosine, butyl ester... 

Representative examples of Arbuzov reactions with alkyl phosphinites and phos-phonites are the preparation of some bisphosphinates (equation 122) functionalized trialkylphosphine oxides (equation 123) and phosphorylated sarcosine analogues (equation 124). Examples involving aryl halides (equation 125) ", a vinyl halide (equation 126) , an alkynyl halide (equation 127) and an acyl halide (equation 128) illustrate the diversity of the reaction. Arbuzov reactions that involve trimethylsilyl phosphinites or phosphonites occur under very mild conditions, usually at or below room temperature, e.g. equation 129 ... 

Some amphoterics containing carboxylic acid functionality, such as the A-alkylami-nopropylglycines, can be analyzed readily by gas chromatography after formation of the methyl esters (97). Sodium lauroyl sarcosinate is readily determined after extraction from soap products with acidic DMF and subsequent derivatization with Ws(trimethylsilyl)-trifluoroacetamide/1% trichloromethylsilane (98). 

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