Hydrochloric Acid → HCID 69103273, compound

HRID 2220379Notes

Reaction equation

HRID 2220379 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:31][C@H:32]([OH:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19]([O:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Na+].Cl>CO.O>[C:1]([O:5][C:6]([N:8]([CH2:31][C@H:32]([OH:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([O:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:15][CH:16]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24823290HCID 24823290, compound

Product 1

HCID 69103273HCID 69103273, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-isopropoxy-4biphenylcarboxylate (1.40 g) in methanol (15 ml)/tetrahydrofuran (6 ml) was added aqueous solution of sodium hydroxide (1N, 7.89 ml) at room temperature and the mixture was stirred at room temperature for 18 hours. The mixture solution was acidified with aqueous hydrochloric acid solution (1N), poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=5/5) to give 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]-ethyl]-3-isopropoxy-4-biphenylcarboxylic acid (1.40 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=5/5)

Sources & evidence

ORD record
ord-925ffeb9be0f40b6ab58cb3cfd9596d3
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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