HCID 178418361, compound → HCID 178431664, compound

HRID 339917Notes

Reaction equation

HRID 339917 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:36])([CH3:35])[CH:23]([C:28]2[CH:29]=[N:30][C:31](Cl)=[CH:32][CH:33]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])(C(C)(C)C)(C)C.[H][H]>CO.[Pd]>[CH3:35][C:22]1([CH3:36])[O:21][C:20]([NH:19][C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:10][CH2:9][OH:8])=[N:25][S:24](=[O:26])(=[O:27])[CH:23]1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178431685HCID 178431685, compound

Product 1

HCID 178431664HCID 178431664, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propyl]-[5-(6-chloropyridin-3-yl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-2-yl]amine (310 mg) in methanol was added palladium on charcoal (5%, 119 mg), and the mixture was stirred in a hydrogen atmosphere for 19 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in methanol (10 ml) and treated with conc. HCl (1 ml). After 2 h, the solution was purified in a purification laboratory by means of preparative HPLC. This gave the product (108 mg) with a molecular weight of 407.5 g/mol (C19H22FN3O4S); MS (ESI): m/e=408 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methanol (10 ml)
  4. additiontreated with conc. HCl (1 ml)
  5. customthe solution was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-ae35e25590c34755b28879655adf6da7
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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