Sodium Bicarbonate → HCID 178522018, compound

HRID 1353880Notes

Reaction equation

HRID 1353880 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

(1R)[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-67bec5890e8c4f67b95bfbe030f71b3f
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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