Benzaldehyde → HCID 58996879, compound

HRID 1040277Notes

Reaction equation

HRID 1040277 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)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.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])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 58996879HCID 58996879, compoundYield 61%

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 (1.78 gm, 14.79 mmol), benzaldehyde (1.77 mL, 17.4 mmol), Et3N (1.21 mL, 8.7 mmol), sodium borohydride (658 mg, 17.4 mmol), and methanol (30 mL) to give 11c (1.5 gm, 61%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 1.19 (3H, t, J=7.08 Hz), 1.88-2.1 (1H, bs), 3.01 (2H, dd, J=0.97, 7.81 Hz), 3.56 (1H, t, J=6.83 Hz), 3.69 (1H, d, J=13.42 Hz), 3.85 (1H, d, J=13.18 Hz), 4.13 (2H, q, J=7.32 Hz), 7.18-7.22 (2H, m), 7.23-7.33 (8H, m). ESI-MS: 284.0 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-ce4c1b28b56647d9955ec492439365d0
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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