Hydrochloric Acid → HCID 58188293, compound

HRID 1845201Notes

Reaction equation

HRID 1845201 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:21][CH:20]([OH:22])[CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23]([O:25]CC)=[O:24])[CH:11]=1)#[N:2].[OH-].[Na+].C(#N)C.Cl>O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:21][CH:20]([OH:22])[CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23]([OH:25])=[O:24])[CH:11]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 58188182HCID 58188182, compound

Product 1

HCID 58188293HCID 58188293, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round-bottom flask was charged with ethyl 2′-cyano-5-(3-hydroxyazetidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylate (25 mg, 0.066 mmol), sodium hydroxide (10 mg, 0.25 mmol), acetonitrile (2 mL) and water (2 mL). The mixture was stirred at room temperature overnight. 1N aq. HCl (3 mL) was added and the volatiles were removed under reduced pressure. The residue was extracted with CH2Cl2, and the CH2Cl2 layer was concentrated to dryness to afford the desired product as a white solid.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. extractionThe residue was extracted with CH2Cl2
  3. concentrationthe CH2Cl2 layer was concentrated to dryness

Sources & evidence

ORD record
ord-3a9fa04e13494506a789c91e6ad45272
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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