Hydrochloric Acid → HCID 86651111, compound

HRID 1810322Notes

Reaction equation

HRID 1810322 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]([C:6]1[CH:7]=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[CH2:26][N:27]([CH2:38][CH3:39])[C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[CH3:5].[OH-].[Li+].OO.Cl>O.C1COCC1>[CH2:31]([NH:30][C:28](=[O:29])[N:27]([CH2:26][C:17]1[CH:18]=[C:19]([C:22]([F:23])([F:24])[F:25])[CH:20]=[CH:21][C:16]=1[C:8]1[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=[C:6]([C@@H:4]([CH3:5])[C:3]([OH:40])=[O:2])[CH:7]=1)[CH2:38][CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 86651110HCID 86651110, compound

Product 1

HCID 86651111HCID 86651111, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-[2′-(3-benzyl-1-ethyl-ureidomethyl)-5,4′-bis-trifluoromethyl-biphenyl-3-yl]-propionic acid methyl ester (0.036 g, 0.06mmol) in 1:1 THF:H2O was added lithium hydroxide (0.005 g, 0.12 mmol) and hydrogen peroxide (29% in water; 0.01 mL, 0.12 mmol). The reaction was stirred at room temperature overnight, and then the mixture was acidified to pH 5 with 10% aqueous HCl. The solution was extracted with EtOAc, and the crude material was purified by preparative HPLC to give the title compound. M+H is 553.

Workup

  1. extractionThe solution was extracted with EtOAc
  2. customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-9573c635f86b43bbb12901414300f782
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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