Hydrochloric Acid → HCID 11555735, compound

HRID 1914306Notes

Reaction equation

HRID 1914306 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][CH2:5][NH:6][C:7](=[O:40])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1.Cl>C1COCC1.[OH-].[Na+].C(OCC)C.O>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:41])=[O:2])=[O:40])=[CH:13][CH:12]=3)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:23][CH:24]=2)=[CH:31][CH:32]=1)([CH3:37])([CH3:38])[CH3:39]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 67153470HCID 67153470, compound

Product 1

HCID 11555735HCID 11555735, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

The 3-(4-{1-[4-(4-tert-Butyl-benzyloxy)-phenoxy]-heptyl}-benzoylamino)-propionic acid methyl ester is dissolved in the THF (1.0 mL) and 5N NaOH (1.0 mL) is added. The mixture is heated to reflux under nitrogen and monitored by HPLC. Upon complete conversion, the reaction is neutralized with 5N HCl (1.0 mL), diluted with diethyl ether and water. The two phases are separated and the organic layer is washed, dried, and concentrated to provide the title compound (80 mg, 0.15 mmol). MS (ES): 544.2 [M−H]−.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureto reflux under nitrogen
  4. customThe two phases are separated
  5. washthe organic layer is washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cd079b0c4fd24d4fa3b87eacd4d6958a
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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