N-Acetyl-D-leucine
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N-Acetyl-D-leucine
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CAS No:
19764-30-8
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Formula:
C8H15NO3
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Chemical Name:
N-Acetyl-D-leucine
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CAS No:
Description
N-acetyl-D-leucine is the N-acetyl derivative of D-leucine. It is a N-acetyl-D-amino acid and a D-leucine derivative. It is a conjugate acid of a N-acetyl-D-leucinate. It is an enantiomer of a N-acetyl-L-leucine.
N-Acetyl-D-leucine Use and Manufacturing
Procedure: The preparation of JV-acetyl-D-Leucine of Compound 10 was carried out by a modified prior art process (/. Am. Chem. Soc, 1951, 73, 3359-3360) as shown in Scheme II below and as described herein.Scheme πA 22 Liter 4-neck vessel was equipped with a thermocouple controller, an overhead mechanic stirrer and two 2.0 Liter addition funnels. The vessel was charged with D.I. HProcedure: A 12 Liter 4-neck vessel was equipped with an overhead mechanical stirrer and a dropping funnel. The vessel was charged with N-acetyl-D-leucine potassium salt (2.95 mol, Compound 10a) (from EXAMPLE 3) and D.I HPreparations of (5)-enantiomer enriched l-(2, 3-dihydrobenzofuran-5-yl)-2, 3, 4, 9- tetrahydro-lH-β-carboline free base mixture and N-acetyl-D-leucine sodium salt EPO A reactor was charged with X (15.0 g), A-ac etyl -D -1 eucine (8.28 g) and zinc oxide (0.31 1 g). Toluene (375 mL) was charged to the reactor followed by 2 -pyri dinecarb oxal d ehy de (183 pL). The mixture was aged at about 55 C for about 6 hrs. and then held at about 35 C for about 4 days. The mixture was cooled to about 0 C and held for about 17 hrs. The product was isolated by filtration and the filter cake was washed with cold toluene (2 x 75 mL). The filter cake was re-charged to the reactor. Ethanol (150 mL) was added and the mixture distilled to remove residual toluene. Once the toluene was removed, the reactor volume was adjusted with ethanol to about 90 mL and the mixture was cooled to about 25 C. Water (210 mL) was added over approximately 10 min. and the mixture aged for approximately 12 hrs. The slurry was filtered and the solids were dried to afford VIII-04. 1H NMR (400 MHz, DMSO-76) d 8.03 (d, J = 8.0 Hz, H i ). 7.95 (d, j= 8.3 Hz, 1H), 7 49 (d, 7 8.3 Hz, 1H), 7.03 (tt, j= 9.5, 2.4 Hz, 1H), 6.87 (dtd, j= 8.4, 6.2, 2.2 Hz, 2H), 5.49 (s, 3H), 4.42 (dd, j= 7.9, 5.9 Hz, 1H), 4.18 (q, j= 7.8 Hz, 1H), 2.93 (dd, j= 13.3, 5.9 Hz, 1H), 2.85 (dd, j= 13.2, 8.0 Hz, 1H), 1.83 (s, 3H), 1.71 - 1.54 (m, I H), 1.47 (dd, j= 8.4, 6.2 Hz, 2H), 0.88 (d, j= 6.6 Hz, 3H), 0.83 (d, j= 6.5 Hz, 3H). 13C NMR (101 MHz, DMSO- ) d 174.72, 169.03, 162.07 (dd, j= 245.5, 13.3 Hz), 161.79, 143.51, 142.82 (t, 7 = 9.4 Hz), 139.72, 128.39, 1 19.30, 1 13.36 - 11 1.39 (m), 101.73 (t, 7 = 25.7 Hz), 55.19, 50.69, 41.74 (d, 7= 2.3 Hz), 40.51, 24.36, 22.91, 22.44, 21.46.
Acetylleucine is a drug used in the treatment of vertigo.
Computed Properties
Molecular Weight:173.21
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:173.10519334
Monoisotopic Mass:173.10519334
Topological Polar Surface Area:66.4
Heavy Atom Count:12
Complexity:177
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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