Hydrochloric Acid → HCID 123912396, compound

HRID 56871Notes

Reaction equation

HRID 56871 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([C:40]2[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=2[C:47]#[N:48])=[CH:34][C:33]1=[O:49])[C:22]([O:24]CC1C=CC=CC=1)=[O:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([C:40]2[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=2[C:47]#[N:48])=[CH:34][C:33]1=[O:49])[C:22]([OH:24])=[O:23])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123319622Benzyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoate

Product 1

HCID 123912396HCID 123912396, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

605 mg (875 μmol) of benzyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoate (racemate) were dissolved in 6 ml of tetrahydrofuran, and 2.2 ml (2.2 mmol, 2.5 eq.) of aqueous sodium hydroxide solution (1.0M) were added. The mixture was stirred at RT for another 1 h and then neutralized with aqueous hydrochloric acid (1N). The phases were separated and the aqueous phase was extracted twice with 25 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product was used for the next step without further purification. Yield: 568 mg (93% of theory)

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with 25 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-d538ff6c113940e8aa473144076f8827
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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