Triethylamine → HCID 24807836, compound

HRID 1040279Notes

Reaction equation

HRID 1040279 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].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11])=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 680234-FluorobenzaldehydeHCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 24807836HCID 24807836, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-leucine methyl ester hydrochloride (2 gm, 11.0 mmol), THF (30 mL), MgSO4 (2.24 gm, 18.7 mmol), 4-fluorobenzaldehyde (2.37 mL, 22.0 mmol), Et3N (1.53 mL, 11.0 mmol), sodium borohydride (833 mg, 22.0 mmol), and methanol (40 mL) to give 11e (1.3 gm, 47%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.84 (3H, d, J=6.59 Hz), 0.9 (3H, d, J=6.59 Hz), 1.47-1.58 (2H, m), 1.76 (1H, heptet), 3.3 (1H, t, J=7.32 Hz), 3.63 (1H, d, J=12.93 Hz), 3.72 (3H, s), 3.81 (1H, d, J=12.93 Hz), 6.99 (2H, t, J=8.78 Hz), 7.32 (2H, dd, J=5.37, 8.3 Hz). ESI-MS: 276.2 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-f133fca42dc84480a245af8ed4463c99
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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