3-prop-2-ynoxypropanoic acid

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

Procedure: 4-t-Butyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2,2]octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-t-butyl-3hydroxymethyloxetane using methodology described in Example I.

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

Procedure: 4-n-Propyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2.2] octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-hydroxymethyl-3-n-propyloxetane using methodology described in Example I.

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

Procedure: 3-(Prop-2-ynyloxy)propionic acid was prepared from propargyl alcohol and ethyl 3-bromopropionate using methodology analogous to that describing the synthesis of 3-(but-3-yn-1-yloxy)propionic acid (Example XIX).

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

Procedure: 4-t-Butyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2,2]octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-t-butyl-3hydroxymethyloxetane using methodology described in Example I.

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

Procedure: 4-n-Propyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2.2] octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-hydroxymethyl-3-n-propyloxetane using methodology described in Example I.

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

Procedure: 3-(Prop-2-ynyloxy)propionic acid was prepared from propargyl alcohol and ethyl 3-bromopropionate using methodology analogous to that describing the synthesis of 3-(but-3-yn-1-yloxy)propionic acid (Example XIX).

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

Procedure: EDC (0.77 g, 4.00 mmol) was added to a solution of tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate (2.00 g, 3.48 mmol), 3-(prop-2-yn-1-yloxy)propanoic acid (0.45 g, 3.48 mmol) and N-hydroxysuccinimide (0.06 g, 0.52 mmol) in DCM (12 mL) at r.t. and the reaction mixture was stirred for 4 hs at room temperature. Upon completion, reaction was concentrated under reduced pressure and purified by silica gel chromatography (EtOAc toEtOAc:MeOH, gradient) to provide 2.12 g (3.10 mmol, 89% yield) of tert-butyl 1-((4-(4-(3-(3-(prop-2-yn-1-yloxy)propanamido)propoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate as slightly yellow oil. Upon completion, reaction was concentrated under reduced pressure purified by silica gel chromatography (EtOAc toEtOAc:MeOH, gradient)

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

Procedure: 4-n-Propyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2.2]octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-hydroxymethyl-3-n-propyloxetane using methodology described in Example I.

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

Procedure: 3-(Prop-2-ynyloxy)propionic acid was prepared from propargyl alcohol and ethyl 3-bromopropionate using methodology analogous to that describing the synthesis of 3-(but-3-yn-1-yloxy)propionic acid (Example XIX).

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

Procedure: 4-t-Butyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2,2]octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-t-butyl-3hydroxymethyloxetane using methodology described in Example I.

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

Procedure: 4-n-Propyl-1-[2-(prop-2-ynyloxy)ethyl]-2,6,7-trioxabicyclo[2.2.2] octane was prepared from 3-(prop-2-ynyloxy)propionic acid and 3-hydroxymethyl-3-n-propyloxetane using methodology described in Example I.

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

Procedure: 3-(Prop-2-ynyloxy)propionic acid was prepared from propargyl alcohol and ethyl 3-bromopropionate using methodology analogous to that describing the synthesis of 3-(but-3-yn-1-yloxy)propionic acid (Example XIX).