Trifluoroacetic acid → HCID 58280539, compound

HRID 238918Notes

Reaction equation

HRID 238918 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[C@@H:10]([NH:25][C@H:26]([C:28]([O:30]C(C)(C)C)=[O:29])[CH3:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:35])[C@@H:10]([NH:25][C@H:26]([C:28]([OH:30])=[O:29])[CH3:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58280543HCID 58280543, compound

Product 1

HCID 58280539HCID 58280539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-((S)-1-tert-butoxycarbonyl-ethylamino)-3-(3′-chloro-biphenyl-4-yl)-propionic acid benzyl ester (1.12 g, 2.27 mmol) in DCM (5 mL) was added TFA (5 mL). After being stirred for 3 hours, the reaction mixture was concentrated and purified by silica gel column chromatography (eluent: 10% MeOH in DCM) to give (S)-2-((S)-1-carboxy-ethylamino)-3-(3′-chloro-biphenyl-4-yl)-propionic acid benzyl ester. MS: m/z (MH+) 438; HPLC retention time 0.73 min (HPLC condition C).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography (eluent: 10% MeOH in DCM)

Sources & evidence

ORD record
ord-ac9091ff77de45eb80e7419acf1e2f46
Source dataset
uspto-grants-2014_02
Patent number
US08642635B2

Reaction notes

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