3-Chloropropanesulphonyl chloride → (5R)-3-(4-(1-(3-Chloropropyl)sulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723803Notes

Reaction equation

HRID 723803 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1.[Cl:27][CH2:28][CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32]>>[Cl:27][CH2:28][CH2:29][CH2:30][S:31]([N:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1)(=[O:33])=[O:32]

Participants

3

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 69364214(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride

Product 1

HCID 69365767(5R)-3-(4-(1-(3-Chloropropyl)sulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

Procedure

(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (380 mg, 1 mM) was treated with 3-chloropropylsulfonyl chloride essentially as in Example 76. After the reaction, the precipitate was filtered, washed with water (10 ml), diethyl ether (2×10 ml), and dried to give the desired product (245 mg).

Workup

  1. customAfter the reaction
  2. filtrationthe precipitate was filtered
  3. washwashed with water (10 ml), diethyl ether (2×10 ml)
  4. customdried

Sources & evidence

ORD record
ord-ccaa86017bad4705b455703929566f8e
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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