benzyl N-[(5S)-5-amino-6-hydroxyhexyl]carbamate

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate, 30 cm3 of trifluoroacetic acid and 20 cm3 of ethanol is stirred at a temperature in the region of 20° C. for 2 hours. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 50 cm3 of water and washed with twice 100 cm3 of diethyl ether. The aqueous phase is separated out after settling has taken place, basified with sodium carbonate to pH 9-10 and then extracted with 3 times 100 cm3 of dichloromethane. The combined extracts are washed with aqueous sodium chloride solution and then dried on magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.0 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate are obtained in the form of a white solid melting at 82° C. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained washed with twice 100 cm3 of diethyl ether The aqueous phase is separated out after settling extracted with 3 times 100 cm3 of dichloromethane The combined extracts are washed with aqueous sodium chloride solution dried on magnesium sulfate filtered concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

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

Procedure: The process is performed as in Example 9, starting with 0.42 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate and 0.24 cm3 of tert-butyl isothiocyanate in 30 cm3 of ethanol at a temperature in the region of 20° C. for 3 days. The reaction is completed by addition of a further 0.48 cm3 of isothiocyanate followed by heating for 1 hour at a temperature in the region of 80° C. After an identical work-up, 0.6 g of ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)-carbothioyl]amino}hexanoate is obtained in the form of a beige-colored oil with a tendency to crystallize. (Rf=0.62 in a 90/10 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate).

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate, 30 cm3 of trifluoroacetic acid and 20 cm3 of ethanol is stirred at a temperature in the region of 20° C. for 2 hours. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 50 cm3 of water and washed with twice 100 cm3 of diethyl ether. The aqueous phase is separated out after settling has taken place, basified with sodium carbonate to pH 9-10 and then extracted with 3 times 100 cm3 of dichloromethane. The combined extracts are washed with aqueous sodium chloride solution and then dried on magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.0 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate are obtained in the form of a white solid melting at 82° C. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained washed with twice 100 cm3 of diethyl ether The aqueous phase is separated out after settling extracted with 3 times 100 cm3 of dichloromethane The combined extracts are washed with aqueous sodium chloride solution dried on magnesium sulfate filtered concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

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

Procedure: The process is performed as in Example 9, starting with 0.42 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate and 0.24 cm3 of tert-butyl isothiocyanate in 30 cm3 of ethanol at a temperature in the region of 20° C. for 3 days. The reaction is completed by addition of a further 0.48 cm3 of isothiocyanate followed by heating for 1 hour at a temperature in the region of 80° C. After an identical work-up, 0.6 g of ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)-carbothioyl]amino}hexanoate is obtained in the form of a beige-colored oil with a tendency to crystallize. (Rf=0.62 in a 90/10 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate).

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate, 30 cm3 of trifluoroacetic acid and 20 cm3 of ethanol is stirred at a temperature in the region of 20° C. for 2 hours. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 50 cm3 of water and washed with twice 100 cm3 of diethyl ether. The aqueous phase is separated out after settling has taken place, basified with sodium carbonate to pH 9-10 and then extracted with 3 times 100 cm3 of dichloromethane. The combined extracts are washed with aqueous sodium chloride solution and then dried on magnesium sulphate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.0 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate are obtained in the form of a white solid melting at 82° C. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained washed with twice 100 cm3 of diethyl ether The aqueous phase is separated out after settling extracted with 3 times 100 cm3 of dichloromethane The combined extracts are washed with aqueous sodium chloride solution dried on magnesium sulphate filtered concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

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

Procedure: The process is performed as in Example 9, starting with 0.42 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate and 0.24 cm3 of tert-butyl isothiocyanate in 30 cm3 of ethanol at a temperature in the region of 20° C. for 3 days. The reaction is completed by addition of a further 0.48 cm3 of isothiocyanate followed by heating for 1 hour at a temperature in the region of 80° C. After an identical work-up, 0.6 g of ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)-carbothioyl]amino}hexanoate is obtained in the form of a beige-colored oil with a tendency to crystallize. (Rf=0.62 in a 90/10 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate).

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 g of benzyl (5S)-5-{[(tert-butyloxy)carbonyl]amino}-6-hydroxyhexylcarbamate, 30 cm3 of trifluoroacetic acid and 20 cm3 of ethanol is stirred at a temperature in the region of 20° C. for 2 hours. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 50 cm3 of water and washed with twice 100 cm3 of diethyl ether. The aqueous phase is separated out after settling has taken place, basified with sodium carbonate to pH 9-10 and then extracted with 3 times 100 cm3 of dichloromethane. The combined extracts are washed with aqueous sodium chloride solution and then dried on magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.0 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate are obtained in the form of a white solid melting at 82° C. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained washed with twice 100 cm3 of diethyl ether The aqueous phase is separated out after settling extracted with 3 times 100 cm3 of dichloromethane The combined extracts are washed with aqueous sodium chloride solution dried on magnesium sulfate filtered concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

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

Procedure: The process is performed as in Example 9, starting with 0.42 g of benzyl (5S)-5-amino-6-hydroxyhexylcarbamate and 0.24 cm3 of tert-butyl isothiocyanate in 30 cm3 of ethanol at a temperature in the region of 20° C. for 3 days. The reaction is completed by addition of a further 0.48 cm3 of isothiocyanate followed by heating for 1 hour at a temperature in the region of 80° C. After an identical work-up, 0.6 g of ethyl (2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butylamino)-carbothioyl]amino}hexanoate is obtained in the form of a beige-colored oil with a tendency to crystallize. (Rf=0.62 in a 90/10 by volume mixture of dichloromethane/methanol, on a Merck 60F254R silica plate).