(5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-one → (5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(2-oxo-3H-1,3,4-thiadiazol-3-ylmethyl)oxazolidin-2-one

HRID 723778Notes

Reaction equation

HRID 723778 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([N:21]3[CH2:25][C@H:24]([CH2:26]O)[O:23][C:22]3=[O:28])=[CH:16][C:15]=2[F:29])=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:30]1[CH:34]=[N:33][NH:32][C:31]1=[O:35]>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([N:21]3[CH2:25][C@H:24]([CH2:26][N:32]4[N:33]=[CH:34][S:30][C:31]4=[O:35])[O:23][C:22]3=[O:28])=[CH:16][C:15]=2[F:29])=[CH:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 11304129(5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-oneHCID 128162731,3,4-Thiadiazol-2-ol

Product 1

HCID 69365819(5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(2-oxo-3H-1,3,4-thiadiazol-3-ylmethyl)oxazolidin-2-oneYield 30.1%

Procedure

Essentially the procedure of Example 35 was used, but starting with (5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-hydroxymethyloxazolidin-2-one (800 mg, 2 mM), and 3H-1,3,4-thiadiazol-2-one (214 mg, 2.2 mM, Helv. Chim. Acta, 1982, 65, 2606), and stirring the reaction for 18 hours. After elution from the SCX column, the gum after evaporation was triturated with diethyl ether to give the desired product (291 mg).

Workup

  1. customthe reaction for 18 hours
  2. washAfter elution from the SCX column
  3. customthe gum after evaporation
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-e672ff098a254141930928b88ddf3ad4
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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