Furfural → HCID 68941260, compound

HRID 1040290Notes

Reaction equation

HRID 1040290 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=O.CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][NH:6][C@@H:5]([C@@H:7]([CH3:8])[CH2:9][CH3:10])[C:4]([O:3][CH3:2])=[O:11]

Participants

8

Reactant 5

HCID 7362FurfuralHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 11171351Isoleucine methyl ester hydrochloride

Product 1

HCID 68941260HCID 68941260, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-isoleucine methyl ester hydrochloride (2.5 gm, 1 equiv), THF (30 mL), MgSO4 (2.8 gm, 1.7 equiv), 2-furaldehyde (2.27 mL, 2 equiv), and Et3N (1.91 mL, 1 equiv), sodium borohydride (1.04 gm, 2 equiv), and methanol (40 mL) to give 11p (2.2 gm, 71%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.86-0.92 (6H, m), 1.16-1.26 (1H, m), 1.48-1.58 (1H, m), 1.68-1.74 (1H, m), 1.78-1.98 (1H, bs), 3.16 (1H, d, J=5.85 Hz), 3.67 (1H, d, J=14.15 Hz), 3.71 (3H, s), 3.82 (1H, d, J=14.4 Hz), 6.19 (1H, d, J=3.17 Hz), 6.32 (1H, d, J=2.68 Hz), 7.37 (1H, d, J=1.95 Hz). ESI-MS: 248.1 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b7f01ee0cbe042538bacdbfc59d320ee
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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