HCID 131736951, compound → HCID 118016875, compound

HRID 57333Notes

Reaction equation

HRID 57333 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]1[CH2:16][CH2:15][C@@H:14]2[CH2:17][N:11]1[C:12](=[O:26])[N:13]2[O:18]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]1[CH2:16][CH2:15][C@@H:14]2[CH2:17][N:11]1[C:12](=[O:26])[N:13]2[OH:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 131736951HCID 131736951, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 118016875HCID 118016875, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound (V) was reacted with triphenylphosphine (PPh3) in a suitable solvent such as tetrahydrofuran followed by addition of a catalytic amount of water to provide corresponding amine. This amino compound was further treated in situ with di-tert-butyl dicarbonate ((Boc)2O) in presence of a suitable base such as triethylamine to provide an amino protected compound, (2S, 5R)-2-(tert-butoxycarbonylaminomethyl)-6-benzyloxy-7-oxo-1, 6-diaza-bicyclo[3.2.1] octane (VI). The intermediate compound of Formula (VI) was subjected to hydrogenolysis using a catalyst such as 5% or 10% Palladium on carbon in presence of a hydrogen source such as hydrogen gas and in a suitable solvent such as methanol to provide debenzylated compound, (2S, 5R)-2-(tert-butoxycarbonylaminomethy)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1] octane (VII).

Sources & evidence

ORD record
ord-67c69612ee1b45dfae2561655a627a92
Source dataset
uspto-grants-2016_09
Patent number
US09434728B1

Reaction notes

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