Oxalyl chloride → HCID 86635481, compound

HRID 1802983Notes

Reaction equation

HRID 1802983 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=O.C(Cl)(=O)C([Cl:24])=O>CN(C)C=O.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([Cl:24])=[O:20]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 66874934HCID 66874934, compound

Product 1

HCID 86635481HCID 86635481, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 10-(2,6-dimethyl-phenyl)-dec-9-enoic acid (239 mg, 0.87 mmol), oxalyl chloride (0.11 mL, 1.3 mmol), and N,N-dimethylformamide (one drop) in dichloromethane (3 mL) was stirred at room temperature for 2 hours, then volatile material was removed by distillation to afford 10-(2,6-dimethyl-phenyl)-dec-9-enoyl chloride. This was redissolved in dichloromethane, then N,N-diisopropylethylamine (140 mg, 1.04 mmol) was added dropwise, followed by (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride. The reaction mixture was stirred at room temperature for 16 h, then washed with water. The organic layer was evaporated and the residue purified by preparative HPLC to afford (R)-4-dimethylamino-3-[10-(2,6-dimethyl-phenyl)-dec-9-enoylamino]-butyric acid benzyl ester.

Workup

  1. customvolatile material was removed by distillation

Sources & evidence

ORD record
ord-0c1ad597178e4388af898ec975202dfc
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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