Acetic Anhydride → HCID 69805139, compound

HRID 2084977Notes

Reaction equation

HRID 2084977 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][S:18](=O)[C:17]([CH3:23])([CH3:22])[CH:16]2[C:24]([O-:26])=[O:25])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:27](OC(=O)C)(=O)C>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH:20]=[CH:19][S:18][C:17]([CH3:23])([CH3:22])[C@@H:16]2[C:24]([O:26][CH3:27])=[O:25])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 131722545HCID 131722545, compound

Product 1

HCID 69805139HCID 69805139, compound

Procedure

A solution of 1.50 g (3.632 mmol) of methyl(3S)-4-({[4-(2-butynyloxy)phenyl]sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylate-1-oxide in 20 mL of acetic anhydride was heated to reflux for 4 h and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.985 g of methyl(3S)-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-2,2-dimethyl-3,4-dihydro-2H-1,4-thiazine-3-carboxylate as a colorless oil. Electrospray Mass Spec 396.1 (M+H)+.

Workup

  1. temperatureto reflux for 4 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Sources & evidence

ORD record
ord-2da6cd230e6c4f029926ed585fa10273
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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