3-amino-1,1,1-trifluoro-4-phenylbutan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 2-[5-Benzyloxycarbonylamino-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 19, 2.00 g, 4.84 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.11 g, 5.06 mmol), WSCI hydrochloride (1.11 g, 5.79 mmol) and HOBT (1.31 g, 9.69 mmol) in DMF (20 mL) to give 2.66 g (94%) of the target compound as pale-yellow crystals.

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

Procedure: 2-[5-Benzyloxycarbonylamino-6-oxo-2-(4-pyridyl)-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-6-oxo-2-(4-pyridyl)-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 18, 2.66 g, 6.57 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.51 g, 6.89 mmol), WSCI hydrochloride (1.51 g, 7.88 mmol) and HOBT (1.77 g, 13.1 mmol) in DMF (25 mL) to give 3.59 g (94%) of the target compound as pale-yellow crystals.

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

Procedure: 2-[5-Benzyloxycarbonylamino-6-oxo-2-(4-pyridyl)-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-6-oxo-2-(4-pyridyl)-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 18, 2.66 g, 6.57 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.51 g, 6.89 mmol), WSCI hydrochloride (1.51 g, 7.88 mmol) and HOBT (1.77 g, 13.1 mmol) in DMF (25 mL) to give 3.59 g (94%) of the target compound as pale-yellow crystals.

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

Procedure: 2-[5-Benzyloxycarbonylamino-6-oxo-2-(3-pyridyl)-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-6-oxo-2-(3-pyridyl)-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 17, 2.50 g, 6.57 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.51 g, 6.89 mmol), WSCI hydrochloride (1.51 g, 7.88 mmol) and HOBT (1.77 g, 13.1 mmol) in DMF (25 mL) to give 3.58 g (94%) of the target compound as colorless crystals.

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

Procedure: 2-[5-Benzyloxycarbonylamino-2-(3,5-dinitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)-acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-2-(3,5-dinitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 16, mixture with diethyl ether, 3.74 g, 7.08 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.78 g, 8.12 mmol), WSCI hydrochloride (1.63 g, 8.50 mmol) and HOBT (1.91 g, 14.1 mmol) in DMF (25 mL) to give 4.06 g (86%) of the target compound as a dark-brown solid.

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

Procedure: 2-[5-Benzyloxycarbonylamino-2-(3,5-dinitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)-acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-2-(3,5-dinitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 16, mixture with diethyl ether, 3.74 g, 7.08 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 1.78 g, 8.12 mmol), WSCI hydrochloride (1.63 g, 8.50 mmol) and HOBT (1.91 g, 14.1 mmol) in DMF (25 mL) to give 4.06 g (86%) of the target compound as a dark-brown solid.

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

Procedure: 2-[5-Benzyloxycarbonylamino-2-(4-nitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidyl]-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)acetamide was synthesized in the same manner as in Example 1. That is, [5-benzyloxycarbonylamino-2-(4-nitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]acetic acid (title compound in Reference Example 15, 14.2 g, 33.5 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 8.08 g, 36.9 mmol), WSCI hydrochloride (7.71 g, 40.2 mmol) and HOBT (9.05 g, 67.0 mmol) in DMF (120 mL) to give 19.4 g (93%) of the target compound as colorless crystals.