Carbamate compounds containing thiocarbamoyl group and process for preparing the same

(S)-3-Thiocarbamoyl-2-phenyl-1,3-propandiol carbamate, represented by the following structural formula II:

• ##STR12##

(R)-3-Thiocarbamoyl-2-phenyl-1,3-propandiol carbamate, represented by the following structural formula III:

• ##STR13##

2-Phenyl-1,3-propandiol monothiocarbamate, represented by the following structural formula IV:

• ##STR14##

(S)-2-Phenyl-1,3-propandiol monothiocarbamate, represented by the following structural formula V:

• ##STR15##

3-Acetoxy-2-phenylpropanol thiocarbamate, represented by the following structural formula VI:

• ##STR16##

(S)-3-Acetoxy-2-phenylpropanol thiocarbamate, represented by the following structural formula VII:

• ##STR17##

A method for preparing 3-thiocarbamoyl-2-phenyl-1,3-propandiol carbamate, represented by the following structural formula I:

• ##STR18## which comprises treating 2-phenyl-1,3-propandiol monothiocarbamate, represented by the following structural formula IV:
• ##STR19## with phosgene in a mixed solvent of aromatic hydrocarbon and halogenohydrocarbon in the presence of amine base and subsequently with ammonia to prepare 3-thiocarbamoyl-2-phenyl-1,3-propandiol carbamate within a short time in a high yield.

A method for preparing (S)-3-thiocarbamoyl-2-phenyl-1,3-propandiol carbamate, represented by the following structural formula II:

• ##STR20## which comprises treating (S)-2-phenyl-1,3-propandiol monothiocarbamate, represented by the following structural formula V:
• ##STR21## with phosgene in a mixed solvent of aromatic hydrocarbon and halogenohydrocarbon in the presence of amine base and subsequently with ammonia to prepare (S)-3-thiocarbamoyl-2-phenyl-1,3-propandiol carbamate within a short time in a high yield and in a high purity.

A method for preparing (R)-3-thiocarbamoyl-2-phenyl-1,3-propandiol carbamate, represented by the following structural formula III:

• ##STR22## which comprises treating (S)-2-phenyl-1,3-propandiol monocarbamate, represented by the following structural formula VIII:
• ##STR23## with thiophosgene in a mixed solvent of aromatic hydrocarbon and halogenohydrocarbon in the presence of amine base and subsequently with ammonia to prepare (R)-3-thiocarbamoyl-2-phenyl-1,3-propandiol carbamate within a short time in a high yield and in a high purity.

A method for preparing 2-phenyl-1,3-propandiol monothiocarbamate, represented by the following structural formula IV:

• ##STR24## which comprises hydrolysing 3-acetoxy-2-phenylpropanol thiocarbamate, represented by the following structural formula VI:
• ##STR25## in a mixture of sodium hydroxide aqueous solution and ethanol to prepare 2-phenyl-1,3-propandiol monothiocarbamate within a short time in a high yield.

A method for preparing (S)-2-phenyl-1,3-propandiol monothiocarbamate, represented by the following structural formula V:

• ##STR26## which comprises hydrolysing (S)-3-acetoxy-2-phenylpropanol thiocarbamate in a phosphate buffer in the presence of an enzyme to prepare (S)-2-phenyl-1,3-propandiol monothiocarbamate within a short time in a high yield and in a high optical purity.

A method for preparing 3-acetoxy-2-phenylpropanol thiocarbamate, represented by the following structural formula VI:

• ##STR27## which comprises treating 3-acetoxy-2-phenylpropanol with thiophosgene in a mixed solvent of aromatic hydrocarbon and halogenohydrocarbon in the presence of amine base and subsequently with ammonia to prepare 3-acetoxy-2-phenylpropanol thiocarbamate within a short time in a high yield.

A method for preparing (S)-3-acetoxy-2-phenylpropanol thiocarbamate, represented by the following structural formula VII:

• ##STR28## which comprises treating (R)-3-acetoxy-2-phenylpropanol with thiophosgene in a mixed solvent of aromatic hydrocarbon and halogenohydrocarbon in the presence of amine base and subsequently with ammonia to prepare (S)-3-acetoxy-2-phenylpropanol thiocarbamate within a short time in a high yield and in a high optical purity.