Hydrochloric Acid → HCID 59367663, compound

HRID 2079807Notes

Reaction equation

HRID 2079807 reaction equation
[OH-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([NH:16][CH:17]1[CH2:20][N:19]([C:21]2[N:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][N:22]=2)[CH2:18]1)(=[O:15])=[O:14].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CO>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([NH:16][CH:17]1[CH2:20][N:19]([C:21]2[N:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][N:22]=2)[CH2:18]1)(=[O:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59367691HCID 59367691, compound

Product 1

HCID 59367663HCID 59367663, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1M NaOH (10 ml) was added to a solution of ethyl 2-{3-[(2-naphthylsulfonyl)amino]azetidin-1-yl}pyrimidine-5-carboxylate (347 mg, 0.84 mmol) in THF (10 ml) and MeOH (2 ml) and the reaction stirred at r.t. overnight. The reaction mixture was acidified to pH˜2 (2M HCl) before adjusting to pH˜7 with sat. NaHCO3 giving a white precipitate. The reaction was cooled to 0° C. and the precipitate isolated by filtration affording the title compound as a white solid (303 mg, 94%). LCMS purity 97%, m/z 385 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customthe precipitate isolated by filtration

Sources & evidence

ORD record
ord-dafddf9c058b41688dfa64613749d9f3
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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