Phosphoric Acid → HCID 18405465, compound

HRID 1018330Notes

Reaction equation

HRID 1018330 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[O:9][C:10]=1[CH2:11][CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:5])C.[OH-].[Na+].OP(O)(O)=O>C(O)C>[C:13]12([CH2:12][CH2:11][C:10]3[O:9][C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])=[N:7][C:6]=3[C:4]([OH:5])=[O:3])[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:21]3)[CH2:20]1)[CH2:22]2

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 54207249HCID 54207249, compound

Product 1

HCID 18405465HCID 18405465, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from step b (540 mg, 1.37 mmol) in ethanol (48m1) and 2M sodium hydroxide (4.8 ml, 9.60 mmol) were refluxed for 16 h. The resulting hot suspension was acidified (pH=3, 1M H3PO4), the ethanol was evaporated, the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4), and the solvent was evaporated to afford the product as a white solid (460 mg, 92%). 1H NMR (300 MHz, CDCl3) 8.00 (1H, d), 7.33 (3H, m), 3.11 (2H, m), 2.70 (3H, s), 2.00 (3H, s), 1.77-1.49 (14H, m).

Workup

  1. customthe ethanol was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-111d05923f344edda513e6990b00c3ff
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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