Acetonitrile--water (1/1) → HCID 131719992, compound

HRID 54819Notes

Reaction equation

HRID 54819 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:23][CH2:22][CH2:21][C@H:4]1[S:5][C:6]1[CH:12]([CH3:13])[CH:11]2[N:8]([C:9](=[O:17])[CH:10]2[CH:14]([OH:16])[CH3:15])[C:7]=1[C:18]([OH:20])=[O:19].P([O-])(O)(O)=O.[Na+].[C:30](#[N:32])[CH3:31].[OH2:33].[H][H]>O1CCOCC1.[Pd]>[NH2:32][CH:30]([CH:3]([CH3:2])[CH2:4][CH3:21])[C:31]([NH:1][CH2:2][C@H:3]1[O:23][CH2:22][CH2:21][C@H:4]1[S:5][C:6]1[CH:12]([CH3:13])[CH:11]2[N:8]([C:9](=[O:17])[CH:10]2[CH:14]([OH:16])[CH3:15])[C:7]=1[C:18]([OH:20])=[O:19])=[O:33]

Participants

7

Reactant 4

HCID 18373917Acetonitrile--water (1/1)HCID 23672064Monosodium phosphate2×HCID 677074071-Amino-2,5-anhydro-3-S-[2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-1,4-dideoxy-3-thio-D-threo-pentitolHCID 178418361HCID 178418361, compound

Product 1

HCID 131719992HCID 131719992, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

The title compound is prepared by the procedure of Example 257 using 0.342 g of product from Example 192 in 10 ml of pH 7 0.1M sodium dihydrogen phosphate buffer, 0.407 g of product from Example 299 in 7 ml of dioxane to give after chromatography (Reverse Phase plates: 25% acetonitrile/water) an oil. The oil is mixed with 0.10 g of 10% palladium on carbon, 10 ml of pH 7 0.1M sodium dihydrogen phosphate buffer and 5 ml of dioxane. The solution is reduced in a Parr apparatus at 47 psi of hydrogen for 3 hours, The reaction mixture is filtered, the filtrate is concentrated in vacuo to a small volume and purified by chromatography (Reverse phase plates: 25% acetonitrile/water) to give 0.090 g of the desired product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo to a small volume
  3. custompurified by chromatography (Reverse phase plates: 25% acetonitrile/water)

Sources & evidence

ORD record
ord-121431a176514971af03680cb9a107b6
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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