Hydrochloric Acid → HCID 67208812, compound

HRID 1945092Notes

Reaction equation

HRID 1945092 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 concentrated. 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. concentrationthe reaction mixture was concentrated
  7. customThe residue is used for a next step without further purification

Sources & evidence

ORD record
ord-9a90f340222b4778b8fd218f334c4a6a
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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