Sodium Carbonate → HCID 131728681, compound

HRID 1363389Notes

Reaction equation

HRID 1363389 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26](C#N)[CH2:25][C@H:24]1[O:31]C(=O)C.C([O-])([O-])=O.[Na+].[Na+]>OP(O)(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@H:24]1[OH:31]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 131728680HCID 131728680, compound

Product 1

HCID 131728681HCID 131728681, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
25 °C

Procedure

Compound of example 127 (2 g, 4.14 mmol) was stirred with H3PO4 (6N, 50 mL) at 100° C. for 1.5 h. The solution was cooled to 25° C. and poured onto ice (100 g). It was made basic using a saturated aqueous Na2CO3 solution and extracted with EtOAc (3×150 mL). The organic extract was washed with water, dried (anhydrous Na2SO4), and concentrated. The crude obtained was purified using a silica gel column and 10% methanol+1% liquor NH3 in CHCl3 as eluant to furnish the title compound.

Workup

  1. additionpoured onto ice (100 g)
  2. extractionextracted with EtOAc (3×150 mL)
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customThe crude obtained
  8. customwas purified

Sources & evidence

ORD record
ord-66eaea092c4e4d57b30af738d40cf1c5
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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