Indolmycin
Title: Indolmycin
CAS Registry Number: 21200-24-8
CAS Name: (5S)-5-[(1R)-1-(1H-Indol-3-yl)ethyl]-2-(methylamino)-4(5H)-oxazolone
Additional Names: (1R,5S)-5-(1-indol-3-ylethyl)-2-(methylamino)-2-oxazolin-4-one; 2-methylamino-5a-(b-indolyl)ethyl-2-oxazolin-4-one
Manufacturers' Codes: PA-155A
Molecular Formula: C14H15N3O2
Molecular Weight: 257.29
Percent Composition: C 65.35%, H 5.88%, N 16.33%, O 12.44%
Literature References: Antibiotic substance produced by Streptomyces albus: Rao, Antibiot. Chemother. 10, 312 (1960); Marsh et al., ibid. 316; GB 862685 (1961 to Pfizer). Structure: M. Schach von Wittenau, H. Els, J. Am. Chem. Soc. 83, 4678 (1961). Total synthesis: eidem, ibid. 85, 3425 (1963); Preobrazhenskaya et al., Tetrahedron 24, 6131 (1968); T. Takeda, T. Mukaiyama, Chem. Lett. 1980, 163. Abs config: T. H. Chan, R. K. Hill, J. Org. Chem. 35, 3519 (1970). Biosynthetic studies: Hornemann et al., Chem. Commun. 1969, 245; eidem, J. Am. Chem. Soc. 93, 3028 (1971).
Properties: Long rectangular prisms from methanol or ethyl acetate, mp 209-210°. [a]D25 -214° (c = 2 in methanol). uv max: 218 nm (E1%1cm 1960). Weakly basic, stable to heat. Slightly sol in water, benzene, ether; moderately in lower alcohols, acetone.
Melting point: mp 209-210°
Optical Rotation: [a]D25 -214° (c = 2 in methanol)
Absorption maximum: uv max: 218 nm (E1%1cm 1960)

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