Diisopropylethylamine → (5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 1452602Notes

Reaction equation

HRID 1452602 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3[CH2:17][CH2:18][N:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][CH:21]=3)=[C:11]([F:29])[CH:10]=2)[CH2:4]1.C(N(C(C)C)CC)(C)C.C1(C)C(S([NH:48][N:49]=[C:50]([CH3:54])[CH:51](Cl)Cl)(=O)=O)=CC=CC=1>C(OCC)(=O)C>[CH2:22]([N:19]1[CH2:18][CH:17]=[C:16]([C:12]2[C:13]([F:15])=[CH:14][C:9]([N:5]3[CH2:4][C@H:3]([CH2:2][N:1]4[CH:51]=[C:50]([CH3:54])[N:49]=[N:48]4)[O:7][C:6]3=[O:8])=[CH:10][C:11]=2[F:29])[CH2:21][CH2:20]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57526982(5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]oxazolidin-2-one2×HCID 865980671,1-Dichloroacetone toluenesulfonylhydrazone

Product 1

HCID 10367222(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-oneYield 46.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-diflurophenyl]-1,3-oxazolidin-2-one (Intermediate 54) (3.20 g, 8.01 mmol) was reacted with diisopropylethylamine (5.60 ml, 32.04 mmol) and 1,1-dichloroacetone toluenesulfonylhydrazone (2.8 g, 9.6 mmol) as described for Example 3. Chromatography on silica gel with ethyl acetate gave 1.74 g of the title product.

Sources & evidence

ORD record
ord-ddd7b6509243494385681f61b4581c82
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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