Dimethyl Sulfide → HCID 69731969, compound

HRID 982589Notes

Reaction equation

HRID 982589 reaction equation
[CH2:1]([C@@H:8]1[C@@H:16]([OH:17])[C@H:15]([CH3:18])[O:14][C:13](=[O:19])[C@@H:12]([NH:20][C:21]([C:23]2[C:28]([OH:29])=[C:27]([O:30][CH3:31])[CH:26]=[CH:25][N:24]=2)=[O:22])[CH2:11][O:10][C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][S:34][CH3:35].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(#N)C.C(OCC)C.C(OCC)(=O)C.C(O)(=O)C>[CH2:1]([C@@H:8]1[C@@H:16]([O:17][CH2:33][S:34][CH3:35])[C@H:15]([CH3:18])[O:14][C:13](=[O:19])[C@@H:12]([NH:20][C:21]([C:23]2[C:28]([OH:29])=[C:27]([O:30][CH3:31])[CH:26]=[CH:25][N:24]=2)=[O:22])[CH2:11][O:10][C:9]1=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 1068Dimethyl SulfideHCID 7187Benzoyl PeroxideHCID 516892Sodium BicarbonateHCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

Product 1

HCID 69731969HCID 69731969, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

Compound 1b (2.0 g, 4.5 mmol) was dissolved in acetonitrile. Dimethylsulfide (6.6 mL) and acetic acid (2 mL) were added and the resulting mixture cooled to 0-5° C. (ice bath) under nitrogen. Benzoyl peroxide (6.36 g, 26 mmol) was added in several portions over 5 hours, then stirred for an additional 10 minutes, and then the reaction mixture was poured into a mixture of ethyl acetate and saturated aq. sodium bicarbonate (100 mL each). The organic phase was separated, rinsed with water, brine (×2), and concentrated in vacuo to give a gum. This gum upon addition of 50 mL of diethyl ether afforded 1.56 g (70%) of an off a white crystalline solid. m.p.=159-160° C. Spectral data were consistent with the title compound.

Workup

  1. customThe organic phase was separated
  2. washrinsed with water, brine (×2)
  3. concentrationconcentrated in vacuo
  4. customto give a gum
  5. customafforded 1.56 g (70%) of an off a white crystalline solid

Sources & evidence

ORD record
ord-d03077d8da2344eb9438ffc209efac2e
Source dataset
uspto-grants-2005_03
Patent number
US06861390B2

Reaction notes

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