HCID 178418361, compound → HCID 178431651, compound

HRID 2405741Notes

Reaction equation

HRID 2405741 reaction equation
Br[C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C@@H:7]2[C:12]([CH3:14])([CH3:13])[O:11][C:10]([NH:15][C:16]34[CH2:23][CH:22]5[CH2:24][C:18]([C:25]([NH2:27])=[O:26])([CH2:19][CH:20]3[CH2:21]5)[CH2:17]4)=[N:9][S:8]2(=[O:29])=[O:28])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[CH2:6]([C@@H:7]1[C:12]([CH3:14])([CH3:13])[O:11][C:10]([NH:15][C:16]23[CH2:23][CH:22]4[CH2:24][C:18]([C:25]([NH2:27])=[O:26])([CH2:19][CH:20]2[CH2:21]4)[CH2:17]3)=[N:9][S:8]1(=[O:28])=[O:29])[C:5]1[CH:30]=[CH:31][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178431649HCID 178431649, compound

Product 1

HCID 178431651HCID 178431651, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3a-[(R)-5-(4-bromobenzyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-2-ylamino]hexahydro-2,5-methanopentalene-2-carboxamide (80 mg) was dissolved in ethanol and stirred in a hydrogen atmosphere (5 bar) in the presence of palladium on charcoal (10%) for 30 min. The solution was filtered and concentrated. Purification was effected by preparative HPLC. This gave the product (33 mg) with a molecular weight of 431.5 g/mol (C22H29N3O4S), MS (ESI): (M+H+) 432.5 g/mol.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. customPurification

Sources & evidence

ORD record
ord-c05b99fcb1a247c5aa8ba61c79eb8a06
Source dataset
uspto-grants-2014_08
Patent number
US08809325B2

Reaction notes

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