Sodium Bicarbonate → HCID 178522018, compound

HRID 2183323Notes

Reaction equation

HRID 2183323 reaction equation
C([O:4][C@@H:5]([C:12](=[O:59])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29]4[N:33]=[CH:32][N:31](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:30]=4)[CH:27]=3)[N:22](C3CCCCO3)[N:21]=2)[CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.C([O-])(O)=O.[Na+]>Cl.O1CCOCC1>[NH:31]1[CH:32]=[N:33][C:29]([C:26]2[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[C:20]3[C:16]2[CH:15]=[C:14]([NH:13][C:12](=[O:59])[C@H:5]([OH:4])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:19]=[CH:18][CH:17]=2)=[N:30]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 20789001HCID 20789001, compound

Product 1

HCID 178522018HCID 178522018, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(1 R)[N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)carbamoyl]phenylmethyl acetate was dissolved in 4 mL of 4.0 N HCl in 1,4-dioxane and the reaction was stirred at room temperature overnight. Monitoring of the reaction showed that the alcohol functionality had been partially deprotected under these conditions. After neutralization with aqueous NaHCO3 after 48 hours, the crude product was extracted in ethyl acetate. The residue was then dissolved in 2 mL of MeOH and the solution was treated with 0.5 mL of aqueous saturated K2CO3 solution. After 2 hours at room temperature, deprotection was complete. The reaction mixture was neutralized and the crude product extracted with ethyl acetate and purified by preparative HPLC (0.036 g, 35% yield over 3 steps): 1H NMR (CD3OD) δ 8.74, 8.55 (s, 1H), 8.22 (br s, 1H), 8.10 (br s, 2H), 7.78 (dt, 2H), 7.68 (br s, 1H), 7.58 (d, 2H), 7.51 (t, 1H), 7.382-7.30 (m, 3H), 5.21 (s, 1H); ES-MS (m/z) 411 [M+H]+.

Workup

  1. extractionthe crude product was extracted in ethyl acetate
  2. dissolutionThe residue was then dissolved in 2 mL of MeOH
  3. additionthe solution was treated with 0.5 mL of aqueous saturated K2CO3 solution
  4. waitAfter 2 hours at room temperature
  5. extractionthe crude product extracted with ethyl acetate
  6. custompurified by preparative HPLC (0.036 g, 35% yield over 3 steps)

Sources & evidence

ORD record
ord-fd6585f68bad47ecb5db626e34a1b2d4
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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