Hydrochloric Acid → HCID 86589053, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Tri-o-tolylphosphine	HCID 80271	—
Reactant	3-Methylphenylalanine	HCID 2761494	—
Reactant	6-Iodo-3H-isobenzofuran-1-one	HCID 7174166	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Benzyl triethylammonium chloride	HCID 66133	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86589053	HCID 86589053	—

Reaction Steps

A solution of 6-iodophthalide (1.0 g, 3.85 mmol), (S)-3-methylphenylalanine.HCl (0.83 g, 3.85 mmol) K2CO3 (0.53 g, 3.85 mmol), CuI (73 mg, 0.38 mmol), TEBA (0.32 g, 1.3 mmol), tri-o-tolylphosphine (0.23 g, 0.77 mmol), Pd(OAc)2 (86 mg, 0.38 mmol), triethylamine (2.14 mL, 15.38 mmol) and water (1.2 mL) in DMF (12 mL) is heated to 100° C. for 12 h. After cooling, the solution is diluted with EtOAc, and washed with 1 N HCl (100 mL), sat'd LiCl (50 mL) and water (100 mL), evaporated and chromatographed (2% MeOH/CH2Cl2, 0 to 0.05% acetic acid) to yield (S)-6-[(1-carboxy-2-(3-methylphenyl)-ethylamino]-phthalide, as a light brown foam.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06812237B2
Source dataset	uspto-grants-2004_11
ORD ID	ord-3c0cc83bffe2457484d06e064a3139a2
Source note	uspto-grants-2004_11