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Volumn , Issue 2, 2005, Pages 255-258

Trifluoroacetylation of amino acids under aqueous conditions using a readily prepared non-odoriferous reagent

Author keywords

Amino acids; Green chemistry; Schotten baumann; Thioester; Trifluoroacetylation

Indexed keywords

ACETIC ACID DERIVATIVE; AMINO ACID; REAGENT; S DODECYLTRIFLUOROTHIOACETATE; THIOL DERIVATIVE; TRIFLUOROACETIC ACID; TRIFLUOROACETYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 13844269075     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837209     Document Type: Article
Times cited : (6)

References (39)
  • 8
    • 13844272721 scopus 로고    scopus 로고
    • US Pat. 5569781, 1996
    • (g) Kleemiss, W.; Feld, M. US Pat. 5569781, 1996.
    • Kleemiss, W.1    Feld, M.2
  • 14
    • 0003405157 scopus 로고    scopus 로고
    • corrected ed.; Georg Thieme Verlag: Stuttgart
    • (b) Kocienski, P. Protecting Groups, corrected ed.; Georg Thieme Verlag: Stuttgart, 2000, 189-190.
    • (2000) Protecting Groups , pp. 189-190
    • Kocienski, P.1
  • 19
    • 84981751612 scopus 로고
    • (b) The bistrifluoroacetylation of 2,4-diaminoglutaric acid using S-phenyltrifluorothioacetate with aqueous sodium bicarbonate has been reported: Weygand, F.; Spiess, B. Chem. Ber. 1964, 97, 3456.
    • (1964) Chem. Ber. , vol.97 , pp. 3456
    • Weygand, F.1    Spiess, B.2
  • 20
    • 13844272719 scopus 로고    scopus 로고
    • note
    • 4 and concentrated to give TFA-ACC (2) as a white solid (347 mg, 72%).
  • 21
    • 13844297183 scopus 로고    scopus 로고
    • note
    • NaCl-HCl workup solution was prepared by dissolving 22 g of NaCl in 1 L 3 N HCl.
  • 30
    • 13844254611 scopus 로고    scopus 로고
    • note
    • 3): δ = -76.0.
  • 31
    • 13844272720 scopus 로고    scopus 로고
    • note
    • Yield determined by HPLC assay of peak area vs the area of an analytical sample of TFA-ACC.
  • 32
    • 13844254609 scopus 로고    scopus 로고
    • note
    • Borax-NaOH buffer proved ineffective in buffer capacity, often allowing the pH to drop below 8 within 2-3 h.
  • 33
    • 13844281861 scopus 로고    scopus 로고
    • note
    • 4. Concentration of the organic product stream gave N-trifluoroacetylphenylalanine as a white solid (747 mg, 91%).
  • 35
    • 13844271574 scopus 로고    scopus 로고
    • note
    • 6): δ = -74.3.
  • 38
    • 13844276292 scopus 로고    scopus 로고
    • note
    • Precipitate formed with some amino acids when MeCN was added.
  • 39
    • 13844280598 scopus 로고    scopus 로고
    • note
    • Acidification of the reaction mixture formed a biphasic mixture with some amino acids. The top MeCN phase contained the product and was separated before the EtOAc extraction of the aqueous phase. This MeCN phase was combined with the EtOAc extracts before brine wash and drying of the combined organic extracts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.