Hydrochloric Acid → 10-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-dec-4-enoic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Propionic Acid	HCID 1032	—
Reactant	Triethyl orthoacetate	HCID 66221	—
Reactant	[6-Hydroxy-8-(2-methyl-pyrimidin-5-yl)-oct-7-enyl]-carbamic acid tert-butyl ester	HCID 73687171	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	10-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-dec-4-enoic acid ethyl ester	HCID 69666454	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

A solution of 24-4 (1.00 g, 2.98 mmol) in triethyl orthoacetate (50 mL) was treated with propionic acid (2.5 mg, 0.034 mmol) and heated to 150° C. for 3 h. The reaction mixture was cooled to room temperature and treated with 1 N HCl and brine (75 mL each). The mixture was extracted with two portions of ethyl acetate. The combined organics were washed with brine and dried (Na2SO4). Purification via PCTLC (SiO2, 4 mm, 10% EtOH; 90% CH2Cl2) afforded 24-5 (650 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07153862B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-dd95499552944caba5e9f930125ba7e1
Source note	uspto-grants-2006_12