Hydrochloric Acid → HCID 178462022, compound

HRID 331667Notes

Reaction equation

HRID 331667 reaction equation
C([O:3][C:4](=[O:31])[C@@H:5]([NH:7][C@H:8]([C:23](=[O:30])[NH:24][C:25]1[NH:29][N:28]=[N:27][N:26]=1)[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)[CH3:6])C.[OH-].[Na+].Cl>CCO>[Cl:22][C:18]1[CH:17]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][C@H:8]([NH:7][C@@H:5]([CH3:6])[C:4]([OH:31])=[O:3])[C:23](=[O:30])[NH:24][C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178472560HCID 178472560, compound

Product 1

HCID 178462022HCID 178462022, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-[(S)-2-(3′-chloro-biphenyl-4-yl)-1-(1H-tetrazol-5-ylcarbamoyl)-ethylamino]-propionic acid ethyl ester (100 mg, 0.226 mmol) was treated with 2M aqueous NaOH (2 mL) and EtOH (0.5 mL). After stirred at room temperature for 1 hour, the reaction mixture was acidified with 2M HCl to adjust pH 1. The resulted precipitate was collected by filtration. The obtained material was crystallized from EtOH to give (S)-2-[(S)-2-(3′-chloro-biphenyl-4-yl)-1-(1H-tetrazol-5-ylcarbamoyl)-ethylamino]-propionic acid (94 mg).

Workup

  1. filtrationThe resulted precipitate was collected by filtration
  2. customThe obtained material was crystallized from EtOH

Sources & evidence

ORD record
ord-bae76f64caaf46a08fa8a2d055a64ed5
Source dataset
uspto-grants-2014_11
Patent number
US08877786B2

Reaction notes

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