Methanesulfonyl chloride → HCID 53664226, compound

HRID 234236Notes

Reaction equation

HRID 234236 reaction equation
[CH3:1][Si:2]([CH3:41])([C:35]([CH3:40])([CH3:39])[CH:36]([CH3:38])[CH3:37])[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[S:28])[CH2:14][CH2:13][C@@H:12]([CH2:29][OH:30])[CH2:11][O:10][C:9](=[O:31])[C:8]=2[C:7]([CH3:32])=[C:6]([O:33][CH3:34])[CH:5]=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>N1C=CC=CC=1>[CH3:41][Si:2]([CH3:1])([C:35]([CH3:39])([CH3:40])[CH:36]([CH3:37])[CH3:38])[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[S:28])[CH2:14][CH2:13][C@@H:12]([CH2:29][O:30][S:43]([CH3:42])(=[O:45])=[O:44])[CH2:11][O:10][C:9](=[O:31])[C:8]=2[C:7]([CH3:32])=[C:6]([O:33][CH3:34])[CH:5]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57277465HCID 57277465, compound

Product 1

HCID 53664226HCID 53664226, compoundYield 131.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 31 mg of (4R,9S)-16-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-9-hydroxymethyl-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-12-one and 11.5 mg of methanesulfonyl chloride in 0.2 ml of pyridine was stirred at 20° C. for 3 h. The solution was partitioned between dichloromethane and 1M aqueous oxalic acid. The organic layer was washed with brine, dried over sodium sulfate and evaporated in vacuo to yield 46 mg of (4R,9R)-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-9-(methylsulfonyloxymethyl)-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-12-one as an amorphous solid.

Workup

  1. customThe solution was partitioned between dichloromethane and 1M aqueous oxalic acid
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-be3955b289504f23b1a732a77004f9b7
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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