Decanal → HCID 24808004, compound

HRID 1040289Notes

Reaction equation

HRID 1040289 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[CH:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH2:18]([NH:6][C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 5

HCID 8175DecanalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 11600782D-Leucine Methyl Ester Hydrochloride

Product 1

HCID 24808004HCID 24808004, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using D-leucine methyl ester hydrochloride (1.5 gm, 8.25 mmol), THF (20 mL), MgSO4 (1.68 gm, 14.02 mmol), decanal (3.1 mL, 16.5 mmol), Et3N (1.15 mL, 8.25 mmol), sodium borohydride (624 mg, 16.5 mmol), and methanol (30 mL) to give 11o (950 mg, 40%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.86-0.96 (9H, m), 1.2-1.34 (16H, m), 1.38-1.52 (4H, m), 1.69 (1H, heptet), 2.39-2.48 (1H, m), 2.5-2.58 (1H, m), 3.27 (1H, t, J=7.08 Hz), 3.71 (3H, s). ESI-MS: 308.1 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b9daf381168548159291c742998cb173
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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