Water → HCID 9954958, compound

HRID 480389Notes

Reaction equation

HRID 480389 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(OCC)(=O)C.[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 962Water4×HCID 10723809HCID 10723809, compound

Product 1

HCID 9954958HCID 9954958, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 5.064 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 120 ml of ethyl acetate is added 5 ml of water, (about a 4% water:ethyl acetate biphasic solvent mixture) and after standing for about 5 minutes, gives a clear biphasic solvent mixture. An additional 55 ml of water is added followed by 2.5 g of 10% palladium-on-carbon. The reaction mixture is then hydrogenated in a Parr apparatus at 54 psi for 20 hours. The mixture is transferred to a separatory funnel and 100 ml of water is added. The aqueous layer is separated and the ethyl acetate layer washed with 20 ml of water. The combined aqueous layers are filtered through a pad of diatomaceous earth and the pad washed with an additional 30 ml of water. The combined aqueous layers are washed with 200 ml of ethyl acetate and lyophilized to afford 2.3 g(78%) of the desired product. MS (ES), m/z:442.3 (M+H)+, 98.9% area percent pure by analytical HPLC.

Workup

  1. customgives a clear biphasic solvent mixture
  2. customThe mixture is transferred to a separatory funnel
  3. customThe aqueous layer is separated
  4. washthe ethyl acetate layer washed with 20 ml of water
  5. filtrationThe combined aqueous layers are filtered through a pad of diatomaceous earth
  6. washthe pad washed with an additional 30 ml of water
  7. washThe combined aqueous layers are washed with 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-4c5c34be309f468ca42944cd9dfb5426
Source dataset
uspto-grants-2003_11
Patent number
US06649756B2

Reaction notes

Loading…