Hydrochloric Acid → HCID 11555735, compound

HRID 1160892Notes

Reaction equation

HRID 1160892 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-e48c565927c54b0d9552c9dea7dacf30
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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