1-CHLORO-1-ETHENESULFONYL CHLORIDE → HCID 10151157, compound

HRID 1268980Notes

Reaction equation

HRID 1268980 reaction equation
[O:1]=[S:2]1(=[O:25])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]=[N+:21]=[N-:22])[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:4][CH2:3]1.[Cl:26][C:27](S(Cl)(=O)=O)=[CH2:28]>ClCCl>[O:25]=[S:2]1(=[O:1])[CH2:3][CH:4]=[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:28]=[C:27]([Cl:26])[N:22]=[N:21]4)[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 102613831-CHLORO-1-ETHENESULFONYL CHLORIDE2×HCID 11222326HCID 11222326, compound

Product 1

HCID 10151157HCID 10151157, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(azidomethyl)oxazolidin-2-one (Reference Example 2) (1.0 g, 2.7 mmol) and 1-chloro-1-ethenesulfonyl chloride (Intermediate 4) (1.1 g, 6.8 mmol) were heated to 90° C. for one hour with stirring. The reaction mixture was cooled to room temperature, diluted with dichloromethane (10 ml) and applied onto a silica gel column. Elution with hexanes/acetone (1.5:1) gave 0.745 g (64%) of the title compound as a colourless solid.

Workup

  1. washElution with hexanes/acetone (1.5:1)

Sources & evidence

ORD record
ord-7fa0715b715a4676ab24692c9259a45b
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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