Oxalic Acid → HCID 67803488, compound

HRID 2254001Notes

Reaction equation

HRID 2254001 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C@H:23]([OH:44])[CH2:24][N:25]([CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)CC2C=CC=CC=2)[CH:12]=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.[C:45](O)(=[O:49])[C:46]([OH:48])=[O:47]>C(O)C>[C:46]([OH:48])(=[O:47])[C:45]([O:44][C@@H:23]([C:11]1[CH:12]=[CH:13][C:14]([OH:15])=[C:9]([OH:8])[CH:10]=1)[CH2:24][NH:25][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)=[O:49]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 22843638HCID 22843638, compound

Product 1

HCID 67803488HCID 67803488, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1.50 g (2.6 mmole) of the above benzyl-protected amino alcohol (the product of step (c)) in 150 ml ethanol containing 10% dioxane, 400 mg of 10% Pd on carbon atom were added. The reaction mixture was hydrogenated overnight at 25 psi. To the resulting mixture, a solution of 0.23g (2.60 m mole) of oxalic acid in 2 ml ethanol was added. After mixing, the solution was filtered and evaporated under reduced pressure The residue was slurred in ether. The precipitate was collected by filtration, rinsed with ether and then acetone, and dried under vacuum to give 0.570 g of the above-identified product, melting point 158°-162° C. 1H NMR (CD3OD) δ7.0-6.5 (m, 7H, ArH), 4.8 (m, 1H, CHOH), 3.3 (S, 3H, CH3O), 3.00-2.90 (m,4H, CH2N), 2.5-2.4 (m, 2H, ArCH2), 1.6-1.5 (m, 2H, CH2).

Workup

  1. additionAfter mixing
  2. filtrationthe solution was filtered
  3. customevaporated under reduced pressure The residue
  4. filtrationThe precipitate was collected by filtration
  5. washrinsed with ether
  6. dry with materialacetone, and dried under vacuum

Sources & evidence

ORD record
ord-00f5f464efff4d3d84bacb7a53d30794
Source dataset
uspto-grants-1993_08
Patent number
US05234404

Reaction notes

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