Hydrochloric Acid → HCID 178522634, compound

HRID 1628199Notes

Reaction equation

HRID 1628199 reaction equation
[O:1]=[C:2]([NH:25][C:26]1[NH:30][C:29]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[N:28][N:27]=1)[C@@H:3]([N:11]([CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[C:5]1([CH2:4][C@H:3]([NH:11][CH2:19][C:20]2[N:21]=[CH:22][S:23][CH:24]=2)[C:2]([NH:25][C:26]2[NH:30][C:29]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[N:28][N:27]=2)=[O:1])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178453113HCID 178453113, compound

Product 1

HCID 178522634HCID 178522634, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a rt solution of 2.E (147 mg, 0.29 mmol) in dioxane (3.0 mL) was added concentrated HCl (0.5 mL). After stirring at rt for 1.5 hr, the reaction mixture was poured into saturated NaHCO3, diluted with water and extracted with 30% iPrOH/chloroform. The organic solvent was removed under reduced pressure. After purification of the residue by preparative HPLC (10-90% CH3CN/water, 45 min), the combined product fractions was treated with saturated NaHCO3, and extracted with 30% i PrOH/CHCl3. After removal of solvent under reduced pressure, the title product 2 (40 mg, 37%) was obtained as colorless solid. MS ESI (positve.) m/e: 406.1 (M+H); 1H NMR (400 MHz, CD3OD) δ ppm 3.22-3.43 (m, 3H), 3.47-(dd, J=13.50, 6.06 Hz, 1H), 4.40-4.63 (m, 3H), 7.21-7.41 (m, 5H), 7.80 (d, J=1.96 Hz, 1H), 8.50 (d, J=6.65 Hz, 2H), 8.86 (d, J=6.65 Hz, 2H), 9.10 (d, J=1.96 Hz, 1H).

Workup

  1. extractionextracted with 30% iPrOH/chloroform
  2. customThe organic solvent was removed under reduced pressure
  3. customAfter purification of the residue by preparative HPLC (10-90% CH3CN/water, 45 min)
  4. additionthe combined product fractions was treated with saturated NaHCO3
  5. extractionextracted with 30% i PrOH/CHCl3
  6. customAfter removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-b4c1c0049e424a42af0507ba024fb219
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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