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

HRID 604574Notes

Reaction equation

[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

Participants

Reactant 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

Product 1

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

Procedure

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.

Workup

customobtained in Step 1

Sources & evidence

ORD record: ord-e4545a36e8b94747b729f09db6e6f7bf
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910611B2

Reaction notes

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