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

HRID 604578Notes

Reaction equation

HRID 604578 reaction equation
[C:1]([N:4]1[C:8]([CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:7][C:6]([NH:22]C(=O)C(C2C=CC=CC=2)C)=[N:5]1)(=[O:3])[CH3:2].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>>[C:1]([N:4]1[N:5]=[C:6]([NH2:22])[S:7][C:8]1([CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 67039180N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide

Product 1

HCID 67039184N-[2-(3-acetyl-5-amino-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamideYield 51%

Procedure

In the same manner as that in Step 2 of Reference Example 20, from another diastereomer of N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide (0.632 g, 1.33 mmol) eluted later obtained in Step 3 mentioned above, cerium chloride heptahydrate (0.496 g, 1.33 mmol) and sodium borohydride (0.503 g, 13.3 mmol), optically active N-[2-(3-acetyl-5-amino-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamide (232 mg, 51%) was obtained.

Workup

  1. customobtained in Step 3

Sources & evidence

ORD record
ord-e2368f3ec74447d58a89e7148f3c8041
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

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