Hydrochloric Acid → Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid

HRID 1914352Notes

Reaction equation

HRID 1914352 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:22][C:23]2[C:28]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][C:26]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:25][C:24]=2[C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>O1CCCC1.C(OCC)C.O>[C:29]([C:28]1[CH:27]=[C:26]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:25]=[C:24]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:23]=1[O:22][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[O:41])=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:19])[F:20])([CH3:31])([CH3:32])[CH3:30]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67153635Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 67153428Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid methyl ester (0.333 g, 0.500 mmol) is dissolved in tetrahydrofuran (3.0 mL) and sodium hydroxide (3.0 mL, 5N) is added. The reaction is monitored by HPLC, and upon complete conversion, the reaction is neutralized with hydrochloric acid (3.0 mL, 5N) and diluted with diethyl ether and water. The two phases are separated, and the organic layer is washed, dried, and concentrated. The title compound is used without further purification. MS (ES): 652.2 [M−H]−.

Workup

  1. customThe two phases are separated
  2. washthe organic layer is washed
  3. customdried
  4. concentrationconcentrated
  5. customThe title compound is used without further purification

Sources & evidence

ORD record
ord-80e9aee99d89407b85ad8604935eb6ea
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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