Water → HCID 9954958, compound

HRID 480391Notes

Reaction equation

HRID 480391 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:53])[C:7]([S:25][C@@H:26]1[CH2:30][CH2:29][O:28][C@@H:27]1[CH2:31][NH:32][C:33](=[O:52])[C@@H:34]([NH:38]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH:35]([CH3:37])[CH3:36])=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].O>C(O)CCCCC.[Pd]>[NH2:38][C@@H:34]([CH:35]([CH3:37])[CH3:36])[C:33]([NH:32][CH2:31][C@@H:27]1[C@H:26]([S:25][C:7]2[C@H:6]([CH3:53])[C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([OH:14])=[O:13])[CH2:30][CH2:29][O:28]1)=[O:52]

Participants

5

Reactant 2

HCID 962Water2×HCID 10723809HCID 10723809, compound

Product 1

HCID 9954958HCID 9954958, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 81031-HexanolSolvent

Procedure

To a mixture of 0.302 g of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-{[(2R,3R)-2-({[(2S)-3-methyl-2-({[(4-nitrobenzyl)oxy]carbonyl}amino)-butanoyl]amino}methyl)tetrahydrofuran-3-yl]thio}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate in 30 ml of 1-hexanol is added 30 ml of water followed by 0.15 g of 10% palladium-on-carbon. The reaction mixture is then hydrogenated in a Parr apparatus at 54 psi for 23 hours. To the mixture is added 30 ml of water and the mixture is filtered through a pad of diatomaceous earth. The pad is washed with an additional 20 ml of water. The filtrate is transferred to a separatory funnel, the aqueous layer separated and the 1-hexanol layer is washed with 10 ml of water. The combined aqueous layers are washed with 100 ml of ethyl acetate and lyophilized to afford 0.144 g(82%) of the desired product. MS (ES), m/z:442.3 (M+H)+, 99.5% area percent pure by analytical HPLC.

Workup

  1. filtrationthe mixture is filtered through a pad of diatomaceous earth
  2. washThe pad is washed with an additional 20 ml of water
  3. customThe filtrate is transferred to a separatory funnel
  4. customthe aqueous layer separated
  5. washthe 1-hexanol layer is washed with 10 ml of water
  6. washThe combined aqueous layers are washed with 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-f38bbbc8deb544df8190a44ecc49dd11
Source dataset
uspto-grants-2003_11
Patent number
US06649756B2

Reaction notes

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