Acetaldehyde → HCID 24807658, compound

HRID 1040282Notes

Reaction equation

HRID 1040282 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[O-]S([O-])(=O)=O.[Mg+2].[CH:22](=O)[CH3:23].CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH2:22]([NH:7][C@@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([O:4][CH2:2][CH3:3])=[O:15])[CH3:23]

Participants

8

Reactant 5

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 24807658HCID 24807658, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-phenylalanine ethyl ester hydrochloride (2 gm, 8.7 mmol), THF (25 mL), MgSO4 (1.77 gm, 14.79 mmol), acetaldehyde (983 μL, 17.4 mmol), Et3N (1.21 mL, 8.7 mmol), sodium borohydride (658 mg, 17.4 mmol), and methanol (30 mL) to give 11h (900 mg, 47%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 1.1 (3H, t, J=7.13 Hz), 1.15 (3H, t, J=7.13 Hz), 1.42-1.7 (1H, bs), 2.46-2.73 (2H, m), 2.96 (2H, dq, J=7.44, 13.42 Hz), 3.53 (1H, t, J=6.88 Hz), 4.1 (2H, q, J=7.13 Hz), 7.16-7.38 (5H, m). ESI-MS: 244.1 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-89e21f22fb9b4cadb8ab731afb1a6110
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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