Hydrochloric Acid → (2R,4R)-4-Amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic Acid

HRID 508398Notes

Reaction equation

HRID 508398 reaction equation
Cl.C([O:4][C:5](=[O:25])[C@H:6]([OH:24])[CH2:7][C@H:8]([NH2:23])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)C>>[NH2:23][C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)[CH2:7][C@@H:6]([OH:24])[C:5]([OH:25])=[O:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86682253(2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester

Product 1

HCID 86682252(2R,4R)-4-Amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic AcidYield 0.1%

Conditions

Temperature
100 °C

Procedure

1 M aqueous HCl (2.0 mmol) was added to (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (150.0 mg, 431 mmol) and the mixture was stirred at 100° C. for 2 hours. The mixture was concentrated under vacuum for 3 hours and the residue was purified by reverse phase preparative HPLC to yield the title compound (117 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under vacuum for 3 hours
  2. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-9f5833c7517a4010b599df6365f1b38e
Source dataset
uspto-grants-2015_08
Patent number
US09096496B2

Reaction notes

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