Benzaldehyde → HCID 51340338, compound

HRID 1040275Notes

Reaction equation

HRID 1040275 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH2:6].C1COCC1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC.[BH4-].[Na+]>CO>[CH2:17]([NH:6][C@@H:5]([C@@H:7]([CH3:8])[CH2:9][CH3:10])[C:4]([O:3][CH3:2])=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 11171351Isoleucine methyl ester hydrochloride

Product 1

HCID 51340338HCID 51340338, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-isoleucine methyl ester hydrochloride (1 gm, 5.5 mmol), THF (20 mL) MgSO4 (1.12 gm, 9.35 mmol), benzaldehyde (1.12 mL, 11.0 mmol), Et3N (767 μL, 5.5 mmol), sodium borohydride (416 mg, 11.0 mmol), and methanol (30 mL) to give 11a (880 mg, 68%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.88-0.943 (6H, m), 1.16-1.3 (1H, m), 1.55-1.64 (1H, m), 1.68-1.88 (2H, m), 3.13 (1H, d, J=6.10 Hz), 3.62 (1H, d, J=12.93 Hz), 3.74 (3H, s), 3.84 (1H, d, J=12.93 Hz), 7.24-7.29 (1H, m), 7.31-7.39 (4H, m). ESI-MS: 258.0 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-a0315988e9874009b52e480825e6a0d5
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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