Benzoyl-L-phenylalanine

Crystalline

N-benzoyl-L-phenylalanine is an N-acyl-L-phenylalanine that is L-phenylalanine in which one of the hydrogens of the amino group has been replaced by a benzoyl group. It is a N-acyl-L-phenylalanine and a 2-(benzoylamino)-3-phenylpropanoic acid. It is a conjugate acid of a N-benzoyl-L-phenylalaninate. It is an enantiomer of a N-benzoyl-D-phenylalanine.

General procedure: To a stirred solution of compound 3 (490 mg, 1.53 mmol) in TOP (5 mL): water (1 mL) was added LiOH.PLO (90.0 mg, 2 29 mmol) under ice cold condition and the resultant reaction mixture was allowed to stir at room temperature for 3 h. After completion [monitored with LC-MS] reaction mixture was concentrated, resultant crude was diluted with water [50 mL] and washed with EtO Ac [50 mL] Aqueous layer was separated and acidified with l(N) aqueous HC1 up to pH 2-3 and extracted with EtO Ac [50 mLX2] Combined organic layer was washed with brine [30 mL], dried over sodium sulphate and concentrated under reduced pressure to afford Acid C006 (390 mg, Yield: quantitative]. Mass [ESI]: m/z 557.64 [MY-l j.General procedure: Benzoyl chloride (1.2 equiv) was added incrementally in 4 portions over 30 minutes to a solution of the amino acid (1 equiv) and 2.5 M NaOH (3.8 equiv) in distilled water. After the addition was complete, the ice bath was removed, and the reaction was quenched by the dropwise addition of concentrated aqueous hydrochloric acid until pH 1 was reached, which resulted in precipitation of the product. The solid product was isolated by filtration and then recrystallized from water. The resulting crystals were air dried to give the desired N-benzoyl amino acid, which showed no trace of benzoic acid by 1H NMR; S-i (FIG. 8) was produced in 93% yield after isolation (10.86 g, 60.9 mmol) as a white solid. The general procedure A was followed using glycine (5.00 g, 66.6 mmol), benzoyl chloride (9.30 mL, 79.2 mmol), 2.5 M NaOH (100 mL, 251 mmol). 1H-NMR matched that previously reported in the literature (Mesaik et al., 2004).Some Samples used for present invention are as follows: ... S-10: N-benzyloxycarbonyl-L-phenylalanyl-L-tyrosine S-11: N-[(1-naphthoxy)acetyl]-L-phenylalanine S-12: N-[(2-naphthoxy)acetyl]-L-phenylalanine S-13: N-[(4-chlorophenoxy)acetyl]-L-phenylalanine S-14: By way of example, the following derivatized amino acids are prepared by this preparation method: ... N-[9-fluorenylmethyloxycarbonyl]-L-phenylalanine; N-tert-butoxycarbonyl-O-benzyl-L-threonine; N-benzyloxycarbonyl-L-threonine; N-benzyloxycarbonyl-L-alanyl-L-phenylalanine;

Molecular Weight:269.29
XLogP3:2.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:269.10519334
Monoisotopic Mass:269.10519334
Topological Polar Surface Area:66.4
Heavy Atom Count:20
Complexity:331
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes