Hydrochloric Acid → (R)-3-amino-4-(3'-chloro-biphenyl-4-yl)-2-hydroxy-butyric acid methyl ester hydrochloride

HRID 70911Notes

Reaction equation

HRID 70911 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([OH:28])[CH:5]([NH:20]C(OC(C)(C)C)=O)[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.Cl>O1CCOCC1>[ClH:19].[CH3:1][O:2][C:3](=[O:29])[C@H:4]([OH:28])[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67208772(R)-3-tert-butoxycarbonylamino-4-(3'-chloro-biphenyl-4-yl)-2-hydroxy-butyric acid methyl ester

Product 1

HCID 68423710(R)-3-amino-4-(3'-chloro-biphenyl-4-yl)-2-hydroxy-butyric acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-3-tert-butoxycarbonylamino-4-(3′-chloro-biphenyl-4-yl)-2-hydroxy-butyric acid methyl ester (113 mg, 0.269 mmol) is treated with 4M HCl in dioxane (2 mL). After being stirred at room temperature for 1 h, the reaction mixture is concentrated. The residue is used for a next step without further purification. HPLC retention time=1.22, 1.29 minutes (condition A): MS (m+1)=320.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customThe residue is used for a next step without further purification
  3. customHPLC retention time=1.22, 1.29 minutes

Sources & evidence

ORD record
ord-118f630230b34c4089ec34232ea4e540
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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