Triethylamine → Levodopa

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine	HCID 14217229	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	Levodopa	HCID 6047	—

Reaction Steps

2.1 g of p(EG1k-Asp) (1.77 mmol —NH2) was dissolved in 30 mL of DCM and 15 mL of DMF. 842 mg of N-Boc-DOPA (2.83 mmol), 382 mg of HOBt (2.83 mmol), HBTU (2.83 mmol), and 595 μL of Et3N (4.25 mmol) were added. The mixture was stirred for 1 hr at room temperature and added to 450 mL ethyl ether. The polymer was further precipitated in cold MeOH and dried in vacuum to yield 1.9 g of PEE-1 (GPC: Mw=33,800, PD=1.3; UV-vis: 7.7±1.3 wt % DOPA).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08383092B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-e2321beafadf4242989305f3aace3add
Source note	uspto-grants-2013_02