Hydrochloric Acid → HCID 69103161, compound

HRID 2220432Notes

Reaction equation

HRID 2220432 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:36][C@H:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26]CC)=[O:25])=[C:19]([O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([O:5][C:6]([N:8]([CH2:36][C@H:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[C:19]([O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:18]=2)=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86598959HCID 86598959, compound

Product 1

HCID 69103161HCID 69103161, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl [4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-cyclohexyloxy-4-biphenylyl]acetate (441 mg) in ethanol (4.4 ml) was added 1N sodium hydroxide (1.83 ml) at room temperature, and the mixture was stirred at the same temperature for 8 hours. To the resulting mixture was added 1N hydrochloric acid (1.83 ml), and ethanol was removed by evaporation under reduced pressure. To the aqueous mixture was added ethyl acetate and water. After separation, the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform/methanol=100:1 to 20:1) to give [4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-cyclohexyloxy-4-biphenylyl]-acetic acid (359 mg).

Workup

  1. customwas removed by evaporation under reduced pressure
  2. additionTo the aqueous mixture was added ethyl acetate and water
  3. customAfter separation
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform/methanol=100:1 to 20:1)

Sources & evidence

ORD record
ord-041e30d1a95e49a1bbfe6f0c5ff5d850
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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