Oxalyl chloride → HCID 86634494, compound
Reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27](O)=[O:28])[CH:21]=[CH:20]3)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30].C(Cl)(=O)C([Cl:37])=O>>[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27]([Cl:37])=[O:28])[CH:21]=[CH:20]3)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30]Participants
Procedure
Treat a solution of 6-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carboxylic acid (0.11 g, 0.246 mmol) in CH2CL2 (1.0 mL) dropwise with oxalyl chloride (0.13 mL, 1.48 mmol). Stir the solution at RT for 1 h and concentrate to give 6-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carbonyl chloride (“the acid chloride”). Treat a mixture of methylglycine HCl (0.031 g, 0.25 mmol) and Et3N (0.51 mL, 0.37 mmol) in CH2CL2 (3 mL) with a solution of the acid chloride (0.057 g, 0.123 mmol) in CH2CL2 (1 mL). Stir the reaction at RT for 16 h and concentrate. Dissolve the residue in THF (0.5 mL) and MeOH (1.0 mL) and treat with 2N NaOH (0.24 mL, 0.48 mmol). Heat the solution to 50° C. for 16 h, concentrate, dilute with CH2CL2 and water (10 mL each). Acidify the resulting mixture to pH 1 using 5N HCl. Wash the organic layer with brine, dry over Na2SO4, and filter. Concentrate the filtrate and purify by silica gel radial chromatography (10:90 MeOH:CH2CL2) to give the title compound as a white solid (0.021 g, 34%). MS (ES) m/e 504 (M+1).
Workup
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-a0fdb69b787c474e94ad0f86808c751a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943795B2
Reaction notes
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