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

HRID 1452607Notes

Reaction equation

HRID 1452607 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:16][CH2:17][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:19][CH:20]=3)=[C:11]([F:28])[CH:10]=2)[CH2:4]1.C(N(C(C)C)CC)(C)C.C1(C)C(S([NH:47][N:48]=[C:49]([CH3:53])[CH:50](Cl)Cl)(=O)=O)=CC=CC=1.CO>C(OCC)(=O)C>[CH2:21]([N:18]1[CH2:17][CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([N:5]3[CH2:4][C@H:3]([CH2:2][N:1]4[CH:50]=[C:49]([CH3:53])[N:48]=[N:47]4)[O:7][C:6]3=[O:8])=[CH:10][C:11]=2[F:28])[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 11574477(5S)-5-(Aminomethyl)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]oxazolidin-2-one2×HCID 865980671,1-Dichloroacetone toluenesulfonylhydrazone

Product 1

HCID 10366343(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-oneYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-flurophenyl]-oxazolidin-2-one (Intermediate 57) (13 g, 34 mmol) was reacted with diisopropylethylamine (23 ml, 136 mmol) and 1,1-dichloroacetone toluenesulfonylhydrazone (15.1 g, 51 mmol) as described for Example 3. Chromatography on silica gel with 0-5% methanol in ethyl acetate gave 5.17 g of the title product.

Sources & evidence

ORD record
ord-30635bce6e0e4e96810d408b05b3f556
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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