Hydrochloric Acid → HCID 69025476, compound

HRID 1866559Notes

Reaction equation

HRID 1866559 reaction equation
[Si:1]([O:8][C@H:9]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH2:34][OH:35])[CH:28]=1)[CH2:10][NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([O:23]C)=[O:22])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Li+].Cl>O1CCCC1>[Si:1]([O:8][C@H:9]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH2:34][OH:35])[CH:28]=1)[CH2:10][NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57978263HCID 57978263, compound

Product 1

HCID 69025476HCID 69025476, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl {3-[2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]phenyl}acetate (preparation 153), (5 g, 10 mmol) and lithium hydroxide (1M in water, 30 mL, 30 mmol) in tetrahydrofuran (50 mL) was stirred for 48 hours at room temperature. The reaction mixture was then acidified with 1M hydrochloric acid (30 mL), concentrated in vacuo, and the residue was triturated with water and azeotroped (×3) with methanol to afford the title compound as a white solid in 84% yield, 4.1 g.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was triturated with water
  3. customazeotroped (×3) with methanol

Sources & evidence

ORD record
ord-ee779d9d20554d9d882fc53e54ae362c
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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