Hydrochloric Acid → HCID 67208812, compound

HRID 70914Notes

Reaction equation

HRID 70914 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@H:4]([O:21][CH3:22])[CH:5]([NH2:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:9][CH:8]=1.[OH-].[Na+].Cl.O=S(Cl)Cl.[CH3:31]O>>[ClH:19].[CH2:1]([O:2][C:3](=[O:23])[C@H:4]([O:21][CH3:22])[CH:5]([NH2:20])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:11][CH:12]=1)[CH3:31]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 67208840(R)-3-amino-4-(3'-chloro-biphenyl-4-yl)-2-methoxy-butyric acid methyl ester

Product 1

HCID 67208812HCID 67208812, compound

Procedure

To a solution of (R)-3-amino-4-(3′-chloro-biphenyl-4-yl)-2-methoxy-butyric acid methyl ester (500 mg, 1.15 mmol) in MeOH (5 mL) is added 2M NaOH aqueous solution (5 mL). After being stirred at room temperature for 2 h, the reaction mixture is acidified with 2M HCl and extracted with EtOAc. The organic layer is dried over Na2SO4 and concentrated. The residue is dissolved in EtOH (5 mL) and treated with SOCl2 (0.252 mL, 3.26 mmol). After being stirred at 55° C., the reaction mixture was cocentrated. The residue is used for a next step without further purification. HPLC retention time=1.49 minutes (condition A): MS (m+1)=348.2

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in EtOH (5 mL)
  5. stirringAfter being stirred at 55° C.
  6. customThe residue is used for a next step without further purification

Sources & evidence

ORD record
ord-1672101e1e914515a42a5cd35b74ad88
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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