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

HRID 723801Notes

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.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28]>>[CH2:27]([S:29]([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:31])=[O:30])[CH3:28]

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 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 69365470(5R)-3-(4-(1-Ethylsulfonyl-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), was treated with ethanesulfonyl chloride essentially as in Example 77 to give the desired product (21 mg) after chromatography. MS (ESP): 436 (MH+) for C19H22FN5O4S

Sources & evidence

ORD record: ord-d0724a0b8eb445deb67c8e72e91d320a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141583B2

Reaction notes

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