Triethylamine → HCID 24808002, compound

HRID 1040285Notes

Reaction equation

HRID 1040285 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].[C:18]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19](C=O)=[CH:20][CH:21]=[CH:22][CH:23]=1.[CH3:32]CN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[C:26]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:27]=[CH:28][C:29]([CH2:32][NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11])=[CH:30][CH:31]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 24808002HCID 24808002, compoundYield 44%

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 (1.0 gm, 5.5 mmol), THF (25 mL), MgSO4 (1.12 gm, 9.35 mmol), biphenyl carboxaldehyde (2.0 g, 11.0 mmol), Et3N (767 μL, 5.5 mmol), sodium borohydride (417 mg, 11.0 mmol), and methanol (20 mL) to give 11k (750 mg, 44%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.86 (3H, d, J=6.59 Hz), 0.92 (3H d, J=6.59 Hz), 1.49 (2H, dt, J=3.17, 7.07 Hz), 1.7-1.76 (1H, bs), 1.8 (1H, heptet), 3.33 (1H, t, J=7.56 Hz), 3.65 (1H, d, J=12.93 Hz), 3.72 (3H, s), 3.85 (1H, d, J=13.18 Hz), 7.32 (1H, t, J=7.56 Hz), 7.38-7.42 (4H, m), 7.54 (2H, d, J=7.81 Hz), 7.58 (2H, d, J=7.32 Hz). ESI-MS: 312.4 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-591d6951ac464a6cab67cdb8984c05ab
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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