Decanal → HCID 11034987, compound

HRID 1040288Notes

Reaction equation

HRID 1040288 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)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].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])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

8

Reactant 5

HCID 8175DecanalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 11034987HCID 11034987, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-phenyl alanine ethyl ester hydrochloride (1.0 gm, 4.35 mmol), THF (20 mL), MgSO4 (522 mg, 4.35 mmol), decanal (817 μL, 4.35 mmol), Et3N (606 μL, 4.35 mmol), sodium borohydride (330 mg, 8.7 mmol), and methanol (20 mL) to give 11n (270 mg, 19%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.88 (3H, d, J=7.08 Hz), 1.14 (3H, t, J=7.32 Hz), 1.2-1.32 (14H, m), 1.34-1.5 (3H, m), 2.5-2.55 (1H, m), 2.52-2.6 (1H, m), 2.9 (1H, dd, J=7.56, 13.42 Hz), 2.97 (1H, dd, J=6.59, 13.42 Hz), 3.48 (1H, t, J=6.83 Hz), 4.08 (2H, q, J=7.32 Hz), 7.18 (2H, d, J=7.32 Hz), 7.22 (1H, d, J=0.73 Hz), 7.24-7.3 (2H, m). ESI-MS: 334.4 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-f6a155bfa24a44f6a2083bfaec8a891a
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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