2-(tetradecoxymethyl)oxirane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml flask equipped with a stirrer was charged with 5.13 g (14.8 mmol) of 3-(2-hydroxyethylamino)-1-tetradecyloxy-2-propanol prepared from tetradecyl glycidyl ether and ethanolamine in the same manner as in Preparation Example 14, and 70 mol of tetrahydrofuran, 1.95 g (16.9 mmol) of 85% phosphoric acid and 3.54 g (30.7 mmol) of P2O5 were added thereto. The resultant mixture was stirred at 65° C. for 10 hours. After cooling the mixture to room temperature, 0.56 g of water was added to the mixture, stirring was conducted for 30 minutes, 5.0 g of 48% aqueous NaOH were added further. After concentrating the resultant reaction mixture under reduced pressure, the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor. The resultant extract was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel, thereby obtaining 2.32 g (yield: 34.9%) of the title compound monosodium (IIa-14). A 300-ml flask equipped with a stirrer were added After concentrating the resultant reaction mixture under reduced pressure the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor The resultant extract was concentrated under reduced pressure the residue was purified by column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml flask equipped with a stirrer was charged with 5.13 g (14.8 mmol) of 3-(2-hydroxyethylamino)-1-tetradecyloxy-2-propanol prepared from tetradecyl glycidyl ether and ethanolamine in the same manner as in Preparation Example 14, and 70 mol of tetrahydrofuran, 1.95 g (16.9 mmol) of 85% phosphoric acid and 3.54 g (30.7 mmol) of P2O5 were added thereto. The resultant mixture was stirred at 65° C. for 10 hours. After cooling the mixture to room temperature, 0.56 g of water was added to the mixture, stirring was conducted for 30 minutes, 5.0 g of 48% aqueous NaOH were added further. After concentrating the resultant reaction mixture under reduced pressure, the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor. The resultant extract was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel, thereby obtaining 2.32 g (yield: 34.9%) of the title compound monosodium (IIa-14). A 300-ml flask equipped with a stirrer were added After concentrating the resultant reaction mixture under reduced pressure the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor The resultant extract was concentrated under reduced pressure the residue was purified by column chromatography on silica gel

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml two-necked flask equipped with a stirrer was charged with 7.51 g (0.1 mol) of glycine, 8.3 g (0.1 mol) of 48% NaOH and 200 ml of ethanol. While stirring the mixture at 80° C., an ethanol solution of 2.70 g (10 mmol) of tetradecyl glycidyl ether was added, and the resultant mixture was stirred for 3 hours. After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture to acidify it. The mixture was subjected to extraction with chloroform. The resultant extract was concentrated under reduced pressure, and the residue was then purified by column chromatography on silica gel, thereby obtaining 1.17 g (yield: 30.7%) of the title compound [(IIa-10) hydrochloride]. A 300-ml two-necked flask equipped with a stirrer After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture The mixture was subjected to extraction with chloroform The resultant extract was concentrated under reduced pressure the residue was then purified by column chromatography on silica gel

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 25.1 g (0.33 mol) of 3-amino-1-propanol and 6.00 g of ethanol, and the contents were heated and stirred at 80° C. in a nitrogen atmosphere. After 9.00 g (33 mmol) of tetradecyl glycidyl ether were added dropwise over 2 hours, the resultant mixture was stirred further for 1 hour. The reaction mixture was poured into 400 ml of ice water and stirred for 1 hour. Crystals formed were then collected by filtration and recrystallized from methanol, thereby obtaining 15.4 g (yield: 92%) of the title compound (IIa-5). A 300-ml two-necked flask equipped with a stirrer and a dropping funnel the contents were heated stirred for 1 hour Crystals formed were then collected by filtration recrystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml flask equipped with a stirrer was charged with 5.13 g (14.8 mmol) of 3-(2-hydroxyethylamino)-1-tetradecyloxy-2-propanol prepared from tetradecyl glycidyl ether and ethanolamine in the same manner as in Preparation Example 14, and 70 mol of tetrahydrofuran, 1.95 g (16.9 mmol) of 85% phosphoric acid and 3.54 g (30.7 mmol) of P2O5 were added thereto. The resultant mixture was stirred at 65° C. for 10 hours. After cooling the mixture to room temperature, 0.56 g of water was added to the mixture, stirring was conducted for 30 minutes, 5.0 g of 48% aqueous NaOH were added further. After concentrating the resultant reaction mixture under reduced pressure, the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor. The resultant extract was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel, thereby obtaining 2.32 g (yield: 34.9%) of the title compound monosodium (IIa-14). A 300-ml flask equipped with a stirrer were added After concentrating the resultant reaction mixture under reduced pressure the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor The resultant extract was concentrated under reduced pressure the residue was purified by column chromatography on silica gel

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml two-necked flask equipped with a stirrer was charged with 7.51 g (0.1 mol) of glycine, 8.3 g (0.1 mol) of 48% NaOH and 200 ml of ethanol. While stirring the mixture at 80° C., an ethanol solution of 2.70 g (10 mmol) of tetradecyl glycidyl ether was added, and the resultant mixture was stirred for 3 hours. After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture to acidify it. The mixture was subjected to extraction with chloroform. The resultant extract was concentrated under reduced pressure, and the residue was then purified by column chromatography on silica gel, thereby obtaining 1.17 g (yield: 30.7%) of the title compound [(IIa-10) hydrochloride]. A 300-ml two-necked flask equipped with a stirrer After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture The mixture was subjected to extraction with chloroform The resultant extract was concentrated under reduced pressure the residue was then purified by column chromatography on silica gel

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 25.1 g (0.33 mol) of 3-amino-1-propanol and 6.00 g of ethanol, and the contents were heated and stirred at 80° C. in a nitrogen atmosphere. After 9.00 g (33 mmol) of tetradecyl glycidyl ether were added dropwise over 2 hours, the resultant mixture was stirred further for 1 hour. The reaction mixture was poured into 400 ml of ice water and stirred for 1 hour. Crystals formed were then collected by filtration and recrystallized from methanol, thereby obtaining 15.4 g (yield: 92%) of the title compound (IIa-5). A 300-ml two-necked flask equipped with a stirrer and a dropping funnel the contents were heated stirred for 1 hour Crystals formed were then collected by filtration recrystallized from methanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under nitrogen stream, 30 g of sodium ethoxide was added to 851.8 g (18.5 mol) of ethanol, and the mixture was heated to 80° C. Then, 500 g (1.85 mol) of tetradecyl glycidyl ether were added dropwise thereto. The mixture was stirred for 18 hours at the same temperature. Thereafter, ethanol was distilled off, and 10.8 g of 85% phosphoric acid was added thereto, followed by washing the resultant mixture with water three times. After water washing, distillation was performed under reduced pressure, to thereby obtain 446 g of 1-tetradecyl-3-ethylglycerol (yield 76.2%). Thereafter, ethanol was distilled off 10.8 g of 85% phosphoric acid was added by washing the resultant mixture with water three times After water washing, distillation

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml two-necked flask equipped with a stirrer was charged with 7.51 g (0.1 mol) of glycine, 8.3 g (0.1 mol) of 48% NaOH and 200 ml of ethanol. While stirring the mixture at 80° C., an ethanol solution of 2.70 g (10 mmol) of tetradecyl glycidyl ether was added, and the resultant mixture was stirred for 3 hours. After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture to acidify it. The mixture was subjected to extraction with chloroform. The resultant extract was concentrated under reduced pressure, and the residue was then purified by column chromatography on silica gel, thereby obtaining 1.17 g (yield: 30.7%) of the title compound [(IIa-10) hydrochloride]. A 300-ml two-necked flask equipped with a stirrer After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture The mixture was subjected to extraction with chloroform The resultant extract was concentrated under reduced pressure the residue was then purified by column chromatography on silica gel

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 300-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 25.1 g (0.33 mol) of 3-amino-1-propanol and 6.00 g of ethanol, and the contents were heated and stirred at 80° C. in a nitrogen atmosphere. After 9.00 g (33 mmol) of tetradecyl glycidyl ether were added dropwise over 2 hours, the resultant mixture was stirred further for 1 hour. The reaction mixture was poured into 400 ml of ice water and stirred for 1 hour. Crystals formed were then collected by filtration and recrystallized from methanol, thereby obtaining 15.4 g (yield: 92%) of the title compound (IIa-5). A 300-ml two-necked flask equipped with a stirrer and a dropping funnel the contents were heated stirred for 1 hour Crystals formed were then collected by filtration recrystallized from methanol