Trifluoroacetic acid → HCID 59607596, compound

HRID 70853Notes

Reaction equation

HRID 70853 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][C@H:6]([NH:21][C:22](=[O:39])[CH:23]([N:25](C(OC(C)(C)C)=O)[CH2:26][C:27]([O:29]CC)=[O:28])[CH3:24])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[CH:10][CH:9]=1)C.[OH-].[Na+].C(O)(C(F)(F)F)=O>C1COCC1.CO>[C:27]([CH2:26][NH:25][C@@H:23]([CH3:24])[C:22]([NH:21][C@H:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[CH:12][CH:13]=1)[CH2:5][C:4]([OH:40])=[O:3])=[O:39])([OH:29])=[O:28].[C:27]([CH2:26][NH:25][C@H:23]([CH3:24])[C:22]([NH:21][C@H:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[CH:12][CH:13]=1)[CH2:5][C:4]([OH:40])=[O:3])=[O:39])([OH:29])=[O:28]

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59607757HCID 59607757, compound

Product 2

HCID 59607596HCID 59607596, compoundHCID 59607612HCID 59607612, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-[2-(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-propionylamino]-4-(3′-chloro-biphenyl-4-yl)-butyric acid ethyl ester (290 mg, 0.504 mmol) in THF (3 ml) and MeOH (0.5 ml) at room temperature is added 2M NaOH (1.009 ml, 2.017 mmol). The reaction is stirred at room temperature over night. The mixture is concentrated to dryness and the crude i taken up in DCM (3.00 ml), to which is added TFA (3.89 ml, 50.4 mmol) and the mixture is stirred at room temperature for 2 hr. The reaction is concentrated for HPLC purification. Reverse phase HPLC [25 to 50% ACN—H2O (0.1% TFA) over 10 min by Sunfire C18 column] give (R)-3-[(S)-2-(Carboxymethyl-amino)-propionylamino]-4-(3′-chloro-biphenyl-4-yl)-butyric acid and (R)-3-[(R)-2-(Carboxymethyl-amino)-propionylamino]-4-(3′-chloro-biphenyl-4-yl)-butyric acid.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. stirringthe mixture is stirred at room temperature for 2 hr
  3. concentrationThe reaction is concentrated for HPLC purification

Sources & evidence

ORD record
ord-77857c48996343fbb4aa08359901c104
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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