Sodium borohydride → N-[2-(5-amino-2-phenyl-3-propionyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamide

반응식

[CH3:1][S:2]([NH:5][CH2:6][CH2:7][C:8]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:12][C:11]([NH:13]C(=O)C(C2C=CC=CC=2)C)=[N:10][N:9]1[C:24](=[O:27])[CH2:25][CH3:26])(=[O:4])=[O:3].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>>[NH2:13][C:11]1[S:12][C:8]([CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:9]([C:24](=[O:27])[CH2:25][CH3:26])[N:10]=1

참가 물질

반응물 3

HCID 4311764Sodium borohydride

HCID 21585214Cerium trichloride heptahydrate

HCID 67039209N-[5-(2-methanesulfonylaminoethyl)-5-phenyl-4-propionyl-4,5-dihydro-1,3,4-thia-diazol-2-yl]-2-phenylpropanamide

생성물 1

HCID 67039362N-[2-(5-amino-2-phenyl-3-propionyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamide수율 67.1%

실험 절차

In the same manner as that in Step 2 of Reference Example 20, from the one diastereomer of N-[5-(2-methanesulfonylaminoethyl)-5-phenyl-4-propionyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide (4.41 g, 9.03 mmol) eluted later obtained in Step 1 mentioned above, cerium chloride heptahydrate (3.37 g, 9.05 mmol) and sodium borohydride (3.42 g, 90.5 mmol), optically active N-[2-(5-amino-2-phenyl-3-propionyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamide (2.16 g, 67%) was obtained.