Decanal → HCID 24807838, compound

HRID 1040283Notes

Reaction equation

HRID 1040283 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[CH:17](=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH2:17]([NH:6][C@@H:5]([CH:7]([CH3:9])[CH3:8])[C:4]([O:3][CH3:2])=[O:10])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 5

HCID 8175DecanalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 111190Methyl valinate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 24807838HCID 24807838, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-valine methyl ester hydrochloride (1.5 gm, 8.9 mmol), THF (25 mL), MgSO4 (1.81 gm, 15.13 mmol), decanal (3.36 mL, 17.89 mmol), Et3N (1.24 mL, 8.9 mmol), sodium borohydride (677 mg, 17.89 mmol), and methanol (25 mL) to give 11i (1.22 gm, 50%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.87 (3H, t, J=7.07 Hz), 0.92 (3H, d, J=7.37 Hz), 0.94 (3H, d, J=6.83 Hz), 1.2-1.5 (17H, m), 1.88 (1H, sextet), 2.37-2.44 (1H, m), 2.5-2.8 (1H, m), 2.97 (1H, d, J=6.34 Hz), 3.74 (3H, s). ESI-MS: 294.3 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-55917af02211406d9370d6dfb08eb543
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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