6-CHLORO-DL-TRYPTOPHAN

Colourless Prisms

Solid

6-chlorotryptophan is a tryptophan derivative that is tryptophan in which the hydrogen at position 6 of the indole ring has been replaced by a chlorine. It is a tryptophan derivative, a non-proteinogenic alpha-amino acid and an organochlorine compound.

6-Chlorotryptophan A mixture of 20.0 g (0.056 mol) of the compound of and 8 g of Raney nickel in 250 ml. of methanol and 250 ml of tetrahydrofuran was hydrogenated in a rocking autoclave at 1500 psi for 22 hours. The filtered solution was concentrated in vacuo and the crude 6-chlorotryptophan methyl ester (14.4 g. ca. 70% pure) was dissolved in 75 ml of methanol. 4.5 g of sodium hydroxide was added and the mixture was stirred at 50 for 3 hours. The brown solution was again concentrated and the solid residue taken up in 50 ml. of water. 125 ml of ethyl acetate was added and the two phase system was stirred while the aqueous layer was adjusted to pH 5.5 with acetic acid. The mixture was allowed to stand at 0 overnight. The precipitate was collected, washed with ethyl acetate (100 ml), ether (50 ml) and ice cold water (50 ml) and dried to give 8.8 g of crude product. GC-analysis of its tris-trimethylsilyl-derivative confirmed the absence of tryptophan. Recrystallization from glacial acetic acid yielded, after drying at 120/0.1 mm, 7.80 g (58%) of off-white crystals, m.p. 278 (dec.) (lit. 285-286), which was identical with an authentic sample. Anal. Calcd. for C11 H11 N2 O2 Cl: C, 55.36; H, 4.65; N, 11.74; Cl, 14.85. Found: C, 55.45; H, 4.60; N, 11.64; Cl, 14.87.6-Chlorotryptophan A mixture of 60 g (0.16 mol) of the compound of Example 11, and 450 ml. of 2 N aqueous HBr was heated under N2 at 95 for 30 hours. The solution was concentrated in vacuo and the residual salt was taken up in 300 ml of water. The solution was brought to pH 5.5 with 4N NaOH and the mixture was chilled in an icebath for 1 hour. The precipitate was collected, washed with cold water and dried to give 34.8 g of product. Crystallization from glacial acetic acid (360 ml.) afforded, after drying at 100/0.2 mmHg, 30.8 g (82%) of white crystals, m.p. 280 (dec.) (lit. m.p. 285-286), which was identical with an authentic sample. Anal. Calcd. for C11 H11 N2 O2 Cl: C, 55.36; H, 4.65; N, 11.74; Cl, 14.85. Found: C, 55.62; H, 4.66; N, 11.91; Cl, 14.78.

6-Chloro-D,L-tryptophan (cas# 17808-21-8) is a compound useful in organic synthesis.

Molecular Weight:238.67
XLogP3:-0.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:238.0509053
Monoisotopic Mass:238.0509053
Topological Polar Surface Area:79.1
Heavy Atom Count:16
Complexity:275
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes