Sodium Bicarbonate → HCID 22235338, compound

HRID 1743714Notes

Reaction equation

HRID 1743714 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([O:7][CH2:8][CH:9]([OH:26])[CH2:10][N:11]2[CH2:17][CH:16]3[N:18](C(OC(C)(C)C)=O)[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH4+:2].[OH-:7].[CH:16]12[NH:18][CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]([CH2:10][CH:9]([OH:26])[CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:28][CH:27]=1)[CH2:17]2

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 22235399HCID 22235399, compound

Product 2

HCID 14923Ammonium HydroxideHCID 22235338HCID 22235338, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 3-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (3.86 g, 9.96 mmol; from step (a) above) in EtOAc (100 mL) was added HCl/EtOAc (150 mL). The resulting solution was stirred for 2 h and concentrated in vacuo to give a foam. The crude product was neutralised with aqueous NaHCO3, extracted with CH2Cl2 (3×), dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography of the residue on silica gel eluting with CH2Cl2:MeOH:concentrated NH4OH (177:20:3) gave 1.82 g (64%) of the title compound as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a foam
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9b81245a1ba4736bc2d0c11f1309cd4
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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