Hydrochloric Acid → HCID 11703791, compound

HRID 1669265Notes

Reaction equation

HRID 1669265 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][C:17]=2[CH3:28])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>C1COCC1>[CH3:28][C:17]1[CH:18]=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:30])=[O:2])=[O:29])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67341024HCID 67341024, compound

Product 1

HCID 11703791HCID 11703791, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-[4-(3-methyl-biphenyl-4-ylmethoxy)-benzoylamino]-propionic acid methyl ester (0.17 g, 0.42 mmol) and 5M NaOH (2 mL) in THF (4 mL) is heated at 70° C. for 5 h. The mixture is acidified with 5M HCl, and extracted with EtOAc. The organics are washed with water and brine, and dried with MgSO4 to yield the title compound (42 mg, 26%). MS (ES): 390 (M+). The structure is also confirmed by 1H NMR.

Workup

  1. extractionextracted with EtOAc
  2. washThe organics are washed with water and brine
  3. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-54debf7c7ff4491d8b3381e7adfe9845
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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