HCID 178418361, compound → HCID 178453361, compound

HRID 339899Notes

Reaction equation

HRID 339899 reaction equation
[C:1]([O:5][C:6](=[O:46])[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:22]([CH3:24])([CH3:23])[O:21][C:20]([NH:25][C@H:26]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])[CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[N:19][S:18]2(=[O:45])=[O:44])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:46])[NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:22]([CH3:24])([CH3:23])[O:21][C:20]([NH:25][C@H:26]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])[CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:32])[CH3:31])=[N:19][S:18]2(=[O:44])=[O:45])=[CH:13][CH:12]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178453360HCID 178453360, compound

Product 1

HCID 178453361HCID 178453361, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [3-(4-{2-[(S)-3-(tert-Butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamino]-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-5-yl}phenyl)prop-2-ynyl]carbamic acid tert-butyl ester (89 mg) in methanol (25 ml) was added palladium on charcoal (5%, 25 mg), and the solution was stirred in a hydrogen atmosphere for 1 h. The mixture was filtered and the filtrate was concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (49 mg) with a molecular weight of 678.0 g/mol (C34H52FN3O6SSi).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThis was followed by purification by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-39112e1d93464be5bd57433d164694a6
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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