L-Leucine → HCID 86756700, compound

HRID 1977493Notes

Reaction equation

HRID 1977493 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O.[C:11]([OH:15])(=[O:14])[CH:12]=O.[C:16]1(/[CH:22]=[CH:23]/B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:7]([CH:2]([NH:1][C@@H:12]([CH:23]=[CH:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([OH:15])=[O:14])[CH2:3][CH:4]([CH3:6])[CH3:5])([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 6106L-LeucineHCID 5702628Styrylboronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 86756700HCID 86756700, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of L-leucine (100 mg, 0.762 mmol), glyoxylic acid monohydrate (70 mg, 0.762 mmol) and (E)-2-phenylethenyl boronic acid (113 mg, 0.764 mmol) in water (8 mL) was stirred vigorously for 24 hours at 50 C. The precipitate was isolated by filtration, washed with methanol (10 mL) and dried under vacuum to give (E)-2-[(S)-N-(-1′-carboxy-3′-methylbutyl)-amino-4-phenyl-3-butenoic acid (247 mg, 85% yield, 94% de). 1H-NMR (360 MHz, d6-DMSO) δ 7.2-7.5 (m, 5H), 6.62 (d, J=15.3 Hz, 1H), 6.18 (dd, J=15.3 Hz, 8.1 Hz, 1H), 3.82 (d, J=8.1 Hz, 1H), 3.32 (m, 1H), 1.7 (m, 2H), 1.4 (m, 1H), 0.85 (d, 6.8 Hz, 6H).

Workup

  1. customThe precipitate was isolated by filtration
  2. washwashed with methanol (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0405010acdce4ba7bb7580d95b8a1b7f
Source dataset
uspto-grants-2001_05
Patent number
US06232467B1

Reaction notes

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