Triethylamine → HCID 68854963, compound

HRID 1040278Notes

Reaction equation

HRID 1040278 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)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1.CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 115693-MethoxybenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 68854963HCID 68854963, compoundYield 58.2%

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), m-anisaldehyde (2.67 mL, 22.0 mmol), Et3N (1.53 mL, 11.0 mmol), sodium borohydride (833 mg, 22.0 mmol), and methanol (40 mL) to give 11d (1.7 gm, 58%) in FIG. 2. 1H NMR (500 MHz, CD3OD): δ 0.86 (3H, d, J=6.59 Hz), 0.92 (3H, d, J=6.59 Hz), 1.5 (2H, dt, J=2.68, 7.32 Hz), 1.71 (1H, heptet), 3.3 (1H, t, J=7.32 Hz), 3.59 (1H, d, J=13.18 Hz), 3.72 (3H, s), 3.76 (1H, d, J=12.93 Hz), 3.8 (3H, s), 6.82 (1H, dd, J=2.44, 8.29 Hz), 6.89 (1H, d, J=7.56 Hz), 6.93, (1H, t, J=1.95 Hz), 7.23 (1H, t, J=7.81). ESI-MS: 288.2 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-1d6a08e2ca55404ca7768f91a3d6d2ce
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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