tert-butyl N-(5-hydroxypentyl)carbamate

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

Procedure: A solution of 28.6 g of 5-(tert-butoxycarbonylamino)pentan-1-ol in 100 ml of pyridine is cooled to 0° C. and 16.2 g of methanesulfonyl chloride are added dropwise in 3 hours at 0° C. The reaction mixture is stirred overnight at RT and concentrated under vacuum. The residue is taken up with water and extracted with AcOEt, the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 39 g of the expected product, which is used as such in the next step. concentrated under vacuum extracted with AcOEt the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water with a saturated solution of NaCl and dried over sodium sulfate the solvent is evaporated off under vacuum

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

Procedure: Intermediate I-31 was prepared from methyl 5-chloro-2-hydroxybenzoate and tert-butyl 5-hydroxypentylcarbamate analogously to Examples 24-26.

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

Procedure: Intermediate I-31 was prepared from methyl 5-chloro-2-hydroxybenzoate and tert-butyl 5-hydroxypentylcarbamate analogously to Examples 24-26.

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

Procedure: Intermediate I-30 was prepared from methyl 5-chloro-4-fluoro-2-hydroxybenzoate and tert-butyl 5-hydroxypentylcarbamate analogously to Examples 27-28.

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

Procedure: The reaction was carried out under N2 atmosphere. Triphenyl phosphine (0.52 mol) was added to a solution of methyl 4-fluoro-2-hydroxybenzoate (0.47 mol), tert-butyl 5-hydroxypentylcarbamate (0.47 mol) and diisopropyl azodicarboxylate (DIAD; 0.94 mol) in THF (1 l) dropwise at −20° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 h. The resulting mixture was used directly in the next step without further purification. The resulting mixture was used directly in the next step without further purification

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

Procedure: The reaction was carried out under N2 atmosphere. Triphenyl phosphine (0.52 mol) was added to a solution of methyl 4-fluoro-2-hydroxybenzoate (0.47 mol), tert-butyl 5-hydroxypentylcarbamate (0.47 mol) and diisopropyl azodicarboxylate (DIAD; 0.94 mol) in THF (1 l) dropwise at −20° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 h. The resulting mixture was used directly in the next step without further purification. The resulting mixture was used directly in the next step without further purification

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

Procedure: A solution of 28.6 g of 5-(tert-butoxycarbonylamino)pentan-1-ol in 100 ml of pyridine is cooled to 0° C. and 16.2 g of methanesulfonyl chloride are added dropwise in 3 hours at 0° C. The reaction mixture is stirred overnight at RT and concentrated under vacuum. The residue is taken up with water and extracted with AcOEt, the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 39 g of the expected product, which is used as such in the next step. concentrated under vacuum extracted with AcOEt the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water with a saturated solution of NaCl and dried over sodium sulfate the solvent is evaporated off under vacuum

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

Procedure: A solution of 28.6 g of 5-(tert-butoxycarbonylamino)pentan-1-ol in 100 ml of pyridine is cooled to 0° C. and 16.2 g of methanesulfonyl chloride are added dropwise in 3 hours at 0° C. The reaction mixture is stirred overnight at RT and concentrated under vacuum. The residue is taken up with water and extracted with AcOEt, the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 39 g of the expected product, which is used as such in the next step. concentrated under vacuum extracted with AcOEt the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water with a saturated solution of NaCl and dried over sodium sulfate the solvent is evaporated off under vacuum

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

Procedure: tert-Butyl 5-hydroxypentylcarbamate (950 mg, 4.67 mmol) was dissolved in EtOAc, 4-nitrophenyl carbonochloridate (1.130 g, 5.14 mmol) was added, the mixture cooled on an icebath, triethylamine (0.85 mL, 6.07 mmol) was added with stirring and the mixture gradually allowed to reach rt and stirred overnight. The mixture was transferred to a separatory funnel with EtOAc and H2O, and shaken. The organic phase was extracted with 1N HCl, H2O, NAHCO3 (aq., sat.), H2O (twice), brine, dried over Mg2SO4, filtered and concentrated. The residue was purified by chromatography (mixtures of petroleum ether and EtOAc) to afford compound 1. was added to reach rt stirred overnight shaken The organic phase was extracted with 1N HCl, H2O, NAHCO3 (aq., sat.), H2O (twice), brine dried over Mg2SO4 filtered concentrated The residue was purified by chromatography (mixtures of petroleum ether and EtOAc)

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

Procedure: Intermediate I-31 was prepared from methyl 5-chloro-2-hydroxybenzoate and tert-butyl 5-hydroxypentylcarbamate analogously to Examples 24-26.

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

Procedure: Intermediate I-30 was prepared from methyl 5-chloro-4-fluoro-2-hydroxybenzoate and tert-butyl 5-hydroxypentylcarbamate analogously to Examples 27-28.

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

Procedure: The reaction was carried out under N2 atmosphere. Triphenyl phosphine (0.52 mol) was added to a solution of methyl 4-fluoro-2-hydroxybenzoate (0.47 mol), tert-butyl 5-hydroxypentylcarbamate (0.47 mol) and diisopropyl azodicarboxylate (DIAD; 0.94 mol) in THF (1 l) dropwise at −20° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 h. The resulting mixture was used directly in the next step without further purification. The resulting mixture was used directly in the next step without further purification